O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (6-Chloro-pyrazolo[1,5-a]pyrimidin-2-yl)-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-methanone

HRID 571644Notes

Reaction equation

HRID 571644 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:25]=[N:26][C:27]2[N:28]([N:30]=[C:31]([C:33]([OH:35])=O)[CH:32]=2)[CH:29]=1.Cl.[CH3:37][C:38]1[S:39][C:40]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42][C:41]=2[N:47]=1>CN(C=O)C>[Cl:23][C:24]1[CH:25]=[N:26][C:27]2[N:28]([N:30]=[C:31]([C:33]([N:44]3[CH2:45][CH2:46][C:40]4[S:39][C:38]([CH3:37])=[N:47][C:41]=4[CH2:42][CH2:43]3)=[O:35])[CH:32]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226207492-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrochlorideHCID 336956786-Chloropyrazolo[1,5-A]pyrimidine-2-carboxylic acid

Product 1

HCID 71748065(6-Chloro-pyrazolo[1,5-a]pyrimidin-2-yl)-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.72 g (2.23 mmol) TBTU was added to 0.40 g (2.03 mmol) 6-Chloro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid, 0.41 g (2.03 mmol) 2-Methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine hydrochloride and 0.88 mL (6.28 mmol) TEA in 8.0 mL DMF and stirred at RT overnight. The reaction mixture was purified by HPLC chromatography and lyophilized. Yield: 0.18 g (25% of theory). ESI-MS: m/z=348 (M+H)+; Rt(HPLC): 1.01 min. (Method J).

Workup

  1. customThe reaction mixture was purified by HPLC chromatography

Sources & evidence

ORD record
ord-4cc5d84b3729415c9f89bba7c2fff697
Source dataset
uspto-grants-2015_05
Patent number
US09029360B2

Reaction notes

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