5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine → (6-Chloro-pyrazolo[1,5-a]pyrimidin-2-yl)-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-methanone

HRID 571641Notes

Reaction equation

HRID 571641 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[S:14]1[C:23]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][C:17]=2[N:16]=[CH:15]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:20]3[CH2:21][CH2:22][C:23]4[S:14][CH:15]=[N:16][C:17]=4[CH2:18][CH2:19]3)=[O:13])[CH:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 226207475,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineHCID 336956786-Chloropyrazolo[1,5-A]pyrimidine-2-carboxylic acid

Product 1

HCID 71748062(6-Chloro-pyrazolo[1,5-a]pyrimidin-2-yl)-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.19 mL (0.33 mmol, 50%) propane phosphonic acid anhydride was added to 50.0 mg (0.25 mmol) 6-chloropyrazolo[1,5-A]pyrimidine-2-carboxylic acid, 39 mg (0.25 mmol) 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine and 0.12 mL (0.89 mmol) TEA in 1.5 mL DMF and stirred at RT overnight. The reaction mixture was purified by chromatography and lyophilized. Yield: 17 mg (20% of theory). ESI-MS: m/z=334 (M+H)+, Rt(HPLC): 0.79 min (Method M).

Workup

  1. customThe reaction mixture was purified by chromatography

Sources & evidence

ORD record
ord-f6c788e017894a56bf4bd80e24cbca47
Source dataset
uspto-grants-2015_05
Patent number
US09029360B2

Reaction notes

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