Triethylamine → HCID 67958305, compound

HRID 1529358Notes

Reaction equation

HRID 1529358 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH:42]=[C:41]2[C:54]1[CH:59]=[N:58][CH:57]=[C:56]([N:60]2[CH2:65][CH2:64][CH:63]([NH:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH2:62][CH2:61]2)[N:55]=1>C(Cl)Cl>[C:70]([O:69][C:67]([NH:66][CH:63]1[CH2:62][CH2:61][N:60]([C:56]2[N:55]=[C:54]([C:41]3[C:40]4[C:44](=[CH:45][CH:46]=[C:38]([NH:37][C:1](=[O:4])[CH2:2][CH3:3])[CH:39]=4)[N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH:42]=3)[CH:59]=[N:58][CH:57]=2)[CH2:65][CH2:64]1)=[O:68])([CH3:73])([CH3:72])[CH3:71]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67960143HCID 67960143, compound

Product 1

HCID 67958305HCID 67958305, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of propionyl chloride (52.5 mg, 0.708 mmol) in DCM (7 mL) at 0° C. was added Et3N (0.2 mL, 1.47 mmol), HBTU (292 mg, 0.75 mmol), tert-butyl 5-amino-3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-1H-indole-1-carboxylate (300 mg, 0.59 mmol) The resulting reaction mixture was stirred at RT for 3 h. The reaction mixture was extracted with DCM (14 mL), washed with brine, dried over Na2SO4, and concentrated to dryness. The crude product was purified by column chromatography to obtain the title compound (150 mg, 45%) as an off white solid. MS (ESI, pos. ion) m/z: 565.2 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with DCM (14 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ae29c5ed9ea84c2eac75a97fd87649b9
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…