Dimethylformamide → HCID 178517415, compound

HRID 2281919Notes

Reaction equation

HRID 2281919 reaction equation
[F:1][C:2](F)(F)[C:3]1(C(O)=O)CC1.C(Cl)(=O)C([Cl:14])=O.[CH3:17][N:18]([CH:20]=[O:21])C.Cl.[F:23][C:24]1[C:48](F)=[CH:47][CH:46]=[CH:45][C:25]=1[CH2:26][N:27]1[C:31]([C:32]2[CH:36]=[CH:35][O:34][N:33]=2)=[CH:30][C:29](C2N=C(N)C(N)=CN=2)=[N:28]1.ClCCl.[N:53]1C=CC=CC=1>C(Cl)Cl>[Cl-:14].[NH4+:18].[F:1][C:2]1[C:20]([OH:21])=[N:18][C:17]([C:29]2[CH:30]=[C:31]([C:32]3[CH:36]=[CH:35][O:34][N:33]=3)[N:27]([CH2:26][C:25]3[CH:45]=[CH:46][CH:47]=[CH:48][C:24]=3[F:23])[N:28]=2)=[N:53][CH:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 21875418Pyridine methylene chlorideHCID 896572912-(1-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,5-diamine hydrochloride2×

Product 2

HCID 25517Ammonium ChlorideHCID 178517415HCID 178517415, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(trifluoromethyl)cyclopropanecarboxylic acid (0.159 g, 1.03 mmol) in DCM was added oxalyl chloride (0.081 ml, 0.928 mmol) and catalytic DMF. Once gas evolution ceased, this crude reaction mixture was added portion-wise to a suspension of 2-(1-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,5-diamine hydrochloride (Compound 8, 40 mg, 0.100 mmol) in dichloromethane/pyridine (2 ml/2 ml) until complete consumption of starting material was observed by LS/MS. After an ammonium chloride (saturated aqueous) and dichloromethane workup, column chromatography (0-10% MeOH/DCM) provided the desired product as an off-white solid (36%).

Workup

  1. customthis crude reaction mixture
  2. additionwas added portion-wise
  3. customuntil complete consumption of starting material

Sources & evidence

ORD record
ord-e8aa27534d3146e8a56508b79a183f86
Source dataset
uspto-grants-2015_09
Patent number
US09139564B2

Reaction notes

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