6-Chloropicolinic acid → HCID 58386255, compound

HRID 64022Notes

Reaction equation

HRID 64022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH2:23])=[C:16]2[N:15]=1.[Cl:24][C:25]1[N:30]=[C:29]([C:31](O)=[O:32])[CH:28]=[CH:27][CH:26]=1>>[Cl:24][C:25]1[N:30]=[C:29]([C:31]([NH:23][C:22]2[CH:21]=[N:20][N:17]3[CH:18]=[CH:19][C:14]([N:10]4[CH2:11][CH2:12][CH2:13][C@@H:9]4[C:3]4[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=4[F:1])=[N:15][C:16]=23)=[O:32])[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 208126-Chloropicolinic acidHCID 58386314(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine

Product 1

HCID 58386255HCID 58386255, compoundYield 31%

Procedure

Prepared by the method as described in Example 68, substituting (R)-5-(2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine with (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (Preparation B), and substituting picolinic acid with 6-chloropicolinic acid, to provide the final product as a yellowish solid (9.1 mg, 31% yield). MS (apci) m/z=455.2 (M+H).

Workup

  1. customPrepared by the method

Sources & evidence

ORD record
ord-84e8f5180b9b495490ef20d39e06e7c5
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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