4-Chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-7-carboxylic acid → (RS)-1-[(4-Chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-7-yl)carbonyl]azetidine-3-carbonitrile

HRID 930990Notes

Reaction equation

HRID 930990 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([OH:17])=O)[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:18]1[CH2:21][CH:20]([C:22]#[N:23])[CH2:19]1>>[Cl:1][C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([N:18]4[CH2:21][CH:20]([C:22]#[N:23])[CH2:19]4)=[O:17])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 179900774-Chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-7-carboxylic acidHCID 221323843-Azetidinecarbonitrile

Product 1

HCID 90014475(RS)-1-[(4-Chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-7-yl)carbonyl]azetidine-3-carbonitrile

Procedure

150 mg (558 μmol) (RS)-4-chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylic acid (prepared according to intermediate example 31b) were transformed in analogy to example 3 using azetidine-3-carbonitrile to give after working up and purification 72 mg (39%) of the title compound.

Workup

  1. customto give
  2. custompurification 72 mg (39%) of the title compound

Sources & evidence

ORD record
ord-0208405c7d12455eb57da24405d4a77b
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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