Diisopropylethylamine → HCID 58303201, compound

HRID 587392Notes

Reaction equation

HRID 587392 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:37][CH2:36][CH:35]([C:38](O)=[O:39])[CH2:34][CH2:33]2)=[N:30][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:38]([CH:35]3[CH2:36][CH2:37][N:32]([C:29]4[CH:28]=[CH:27][C:26]([CH3:25])=[CH:31][N:30]=4)[CH2:33][CH2:34]3)=[O:39])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16795673HCID 16795673, compoundHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 58303201HCID 58303201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 26.7 mg (0.085 mmol)[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester, 15 mg (0.068 mmol) 1-(5-methyl-2-pyridinyl)-4-piperidinecarboxylic acid (commercially available), 31 mg (0.082 mmol) HATU and 70 uL (0.409 mmol) DIPEA in 2 mL DMF was shaken for 1 h at room temperature. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions the title compound as off-white solid. MS m/e: 551.4 [M]+.

Workup

  1. customThe mixture was subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions the title compound as off-white solid

Sources & evidence

ORD record
ord-e86ebd7f43ba4087b263a578a4d5b48b
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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