Acetic Acid → 2-Amino-6-(3-phenyl-2-propyn-1-yl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

HRID 974327Notes

Reaction equation

HRID 974327 reaction equation
C1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[CH:12]C=O)=CN=1.[NH2:15][C:16]1[S:17][C:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23][C:24]=2[N:25]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[NH2:15][C:16]1[S:17][C:18]2[CH2:19][CH2:20][N:21]([CH2:12][C:11]#[C:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:22][CH2:23][C:24]=2[N:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 199857852-Amino-4,5,6,7,8-pentahydrothiazolo[5,4-d]azepineHCID 545366983-(4-Isoquinolinyl)acrolein

Product 1

HCID 199859652-Amino-6-(3-phenyl-2-propyn-1-yl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from 3-(4-isoquinolinyl)acrolein and 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine by reductive amination with sodium cyanoborohydride (in methanol in the presence of I equivalent of glacial acetic acid). The crude product is purified by column chromatography on silica gel (acetone/methanol/conc. ammonia =50:12:0.5). At first the title compound (A) is eluted. Yield: 4% of theory, Melting point: 205°-208° C. (ether).

Workup

  1. customThe crude product is purified by column chromatography on silica gel (acetone/methanol/conc. ammonia =50:12:0.5)
  2. washAt first the title compound (A) is eluted

Sources & evidence

ORD record
ord-4caae74952694150aff7b8f7f4f97fa9
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

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