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Dimethylformamide → HCID 178464157, compound

HRID 1919183
Notes
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Reaction equation

HRID 1919183 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([N:27]([CH2:38][CH3:39])[C@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29](O)=[O:30])[CH3:26].[CH3:40][CH2:41][N:42]([CH:46]([CH3:48])C)[CH:43]([CH3:45])[CH3:44].[NH:49]1[CH2:53][CH2:52][CH2:51][C@H:50]1[C:54]1[NH:55][CH:56]=[C:57](/[CH:59]=[CH:60]/[C:61]2[CH:66]=[CH:65][C:64](/[CH:67]=[CH:68]/[C:69]3[NH:73][C:72]([C@@H:74]4[CH2:78][CH2:77][CH2:76][NH:75]4)=[N:71][CH:70]=3)=[CH:63][CH:62]=2)[N:58]=1.CN(C=[O:83])C>>[CH2:46]([N:42]([CH2:41][CH3:40])[C@H:43]([C:44]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:45]([N:75]1[CH2:76][CH2:77][CH2:78][C@H:74]1[C:72]1[NH:73][C:69](/[CH:68]=[CH:67]/[C:64]2[CH:63]=[CH:62][C:61](/[CH:60]=[CH:59]/[C:57]3[N:58]=[C:54]([C@@H:50]4[CH2:51][CH2:52][CH2:53][N:49]4[C:29](=[O:30])[C@@H:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:27]([CH2:38][CH3:39])[CH2:25][CH3:26])[NH:55][CH:56]=3)=[CH:66][CH:65]=2)=[CH:70][N:71]=1)=[O:83])[CH3:48]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 81531DiisopropylethylamineHCID 1091378(R)-2-(diethylamino)-2-phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178437181HCID 178437181, compound

Product 1

HCID 178464157
HCID 178464157, compound

Procedure

HATU (76 mg, 0.20 mmol) was added to a stirred solution of (R)-2-(diethylamino)-2-phenylacetic acid (49 mg, 0.20 mmol) in DMF (1 mL) and DIPEA (0.14 mL, 0.80 mmole) and the mixture was stirred for 5 minutes. Then a solution of 1-((E)-2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)vinyl)-4-((E)-2-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)vinyl)benzene (40 mg, 0.10 mmol) in DMF (1 mL) was added and the resulting solution was stirred under argon for 16 hrs. The reaction mixture was purified directly by HPLC and the resulting TFA salt of the desired product was absorbed onto an SCX ion-exchange cartridge with methanol and liberated with a solution of 2 M NH3 in methanol. The fractions containing the desired product were concentrated to yield (1R)-2-((2S)-2-(4-((E)-2-(4-((E)-2-(2-((2S)-1-((2R)-2-(diethylamino)-2-phenylacetyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)vinyl)phenyl)vinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-N,N-diethyl-2-oxo-1-phenylethanamine (35.8 mg) as a pale yellow solid.

Workup

  1. stirringthe resulting solution was stirred under argon for 16 hrs
  2. customThe reaction mixture was purified directly by HPLC
  3. customthe resulting TFA salt of the desired product was absorbed onto an SCX ion-exchange cartridge with methanol
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-ebd791ab52c14c87a2d1a18d6305befd
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618153B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes