Sodium cyanoborohydride → HCID 53856827, compound

HRID 974326Notes

Reaction equation

HRID 974326 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][CH:12]=O)=[CH:2]1.[NH2:14][C:15]1[S:16][C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:23]=2[N:24]=1.C([BH3-])#N.[Na+]>>[NH2:14][C:15]1[S:16][C:17]2[CH2:18][CH2:19][N:20]([CH2:12][CH:11]=[CH:10][C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:21][CH2:22][C:23]=2[N:24]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 199857852-Amino-4,5,6,7,8-pentahydrothiazolo[5,4-d]azepineHCID 540588453-(1H-Indol-3-yl)prop-2-enal

Product 1

HCID 53856827HCID 53856827, compoundYield 11%

Procedure

Prepared from 3-(3-indolyl)acrolein and 1 equivalent of 2-amino-4,5,7,8-tetrahydro-6H- thiazolo[5,4-d]azepine by reductive amination with 0.9 equivalents of sodium cyanoborohydride. Purification of the crude product by column chromatography is carried out using neutral aluminium oxide of activity stage I (toluene/ethyl acetate/ethanol=4:1:0.5). Yield: 11% of theory, Melting point: 155°-160° C.

Workup

  1. customPurification of the crude product by column chromatography

Sources & evidence

ORD record
ord-c7ee4d8ae7cc473cbb94a2f9f3c309ea
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

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