Diisopropylethylamine → 7-Difluoromethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid [5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-amide

HRID 82124Notes

Reaction equation

[F:1][CH:2]([F:16])[C:3]1[N:8]2[N:9]=[C:10]([C:12]([OH:14])=O)[N:11]=[C:7]2[N:6]=[C:5]([CH3:15])[CH:4]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]([C:26]2[C:34]3[CH:33]=[N:32][CH:31]=[N:30][C:29]=3[N:28]([CH:35]([CH3:37])[CH3:36])[CH:27]=2)=[O:25])[CH:21]=[N:22][CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:35]([N:28]1[C:29]2[N:30]=[CH:31][N:32]=[CH:33][C:34]=2[C:26]([C:24]([C:20]2[CH:19]=[C:18]([NH:17][C:12]([C:10]3[N:11]=[C:7]4[N:6]=[C:5]([CH3:15])[CH:4]=[C:3]([CH:2]([F:1])[F:16])[N:8]4[N:9]=3)=[O:14])[CH:23]=[N:22][CH:21]=2)=[O:25])=[CH:27]1)([CH3:37])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

7-Difluoromethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid (29.64 mg, 0.130 mmol) was added to (5-amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (28.1 mg, 0.1 mmol), HATU (49.42 mg, 0.130 mmol) and DIPEA (22.4 uL, 0.13 mmol) in anhydrous DMF (1 mL). The mixture was stirred at 50° C. for 16 hours and then evaporated in vacuo and purified by prep-HPLC (method 5) to afford the title compound in 12% yield, 6.1 mg.

Workup

customevaporated in vacuo
custompurified by prep-HPLC (method 5)

Sources & evidence

ORD record: ord-8c9bbbd93f6f40f2a1c2e9dc23dc075a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

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