Acetic Acid → HCID 86625299, compound

HRID 490626Notes

Reaction equation

HRID 490626 reaction equation
[Cl:1][C:2]([Cl:39])([Cl:38])[CH2:3][O:4][C:5](=[O:37])[N:6]([CH:16]1[CH2:20][CH:19]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])[CH2:25][CH2:24]2)=[O:22])[NH:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15].[F:40][C:41]1[C:48]([F:49])=[CH:47][CH:46]=[CH:45][C:42]=1[CH:43]=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:39][C:2]([Cl:1])([Cl:38])[CH2:3][O:4][C:5](=[O:37])[N:6]([CH:16]1[CH2:20][CH:19]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])[CH2:25][CH2:24]2)=[O:22])[N:18]([CH2:43][C:42]2[CH:45]=[CH:46][CH:47]=[C:48]([F:49])[C:41]=2[F:40])[CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1376642,3-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67546447HCID 67546447, compound

Product 1

HCID 86625299HCID 86625299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {5-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-pyrrolidin-3-yl}-(2,4-difluoro-benzyl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.078 g, 0.13 mmol), 2,3-difluorobenzaldehyde and acetic acid (cat.) in DCM (5 ml) was stirred for 20 min, and then NaBH(OAc)3 (0.041 g, 0.13 mmol) was carefully added. The reaction mixture was stirred overnight, and was concentrated to give crude product which was directly used for next step.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. concentrationwas concentrated
  3. customto give crude product which

Sources & evidence

ORD record
ord-97a84e8e54f547e39e762101db4f1fde
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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