Sodium cyanoborohydride → HCID 178420357, compound

HRID 351163Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[N:2]1.[N+](C1C=CC=CC=1S([N:20]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH:29][CH:30]2[C:39]3[N:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH2:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1)(=O)=O)([O-])=O.C([BH3-])#N.[Na+]>>[N:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[CH2:40][NH:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][N:29]([CH2:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)[CH:30]2[C:39]3[N:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH2:33][CH2:32][CH2:31]2)=[CH:26][CH:27]=1

Participants

Reactant 3

HCID 5003444Sodium cyanoborohydride

HCID 122183831H-Pyrazole-3-carbaldehyde

HCID 22018658N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 178420357HCID 178420357, compoundYield 64.3%

Procedure

Using general procedure A: Reaction of 3-pyrazolecarboxaldehyde (85 mg, 0.88 mmol) and N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (320 mg, 0.589 mmol) with sodium cyanoborohydride (55 mg, 0.883 mmol) followed by purification of the crude material by column chromatography on silica gel (5% methanol in dichloromethane), gave the desired product (166 mg, 45%).

Workup

customfollowed by purification of the crude material by column chromatography on silica gel (5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-e70893a72db84664a22482d4924fa516
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183273B2

Reaction notes

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