Tetrahydrofuran → HCID 178447335, compound

HRID 450342Notes

Reaction equation

HRID 450342 reaction equation
[F:1][C:2]([F:41])([F:40])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[N:27]=[C:26]([NH:28][C:29]4[C:34]([Cl:35])=[C:33]([F:36])[CH:32]=[C:31]([CH2:37][NH2:38])[C:30]=4[Cl:39])[NH:25][C:15]3=[N:16][C:17]=2[N:18]2[CH2:23][CH2:22][CH:21]([F:24])[CH2:20][CH2:19]2)=[O:11])[CH2:5][CH2:4]1.[C:42](Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44].C1COCC1>CO>[F:41][C:2]([F:40])([F:1])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[N:27]=[C:26]([NH:28][C:29]4[C:34]([Cl:35])=[C:33]([F:36])[CH:32]=[C:31]([CH2:37][NH:38][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C:30]=4[Cl:39])[NH:25][C:15]3=[N:16][C:17]=2[N:18]2[CH2:19][CH2:20][CH:21]([F:24])[CH2:22][CH2:23]2)=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 62493Pivaloyl chlorideHCID 178510130HCID 178510130, compound

Product 1

HCID 178447335HCID 178447335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-{2,6-dichloro-5-fluoro-3-(aminomethyl)-phenylamino}-5-[4-fluoro-piperidinyl]-3H-imidazo[4,5-b]pyridine-6-carboxamide (130 mg, 0.210 mmol), pivaloyl chloride (26 μL, 0.21 mmol), TEA (75 mg, 0.74 mmol) and 5 mL THF is stirred for 20 min and diluted with MeOH. The crude product is purified via prep. HPLC (C-18 stable bond, eluent gradient: water(+0.15% HCOOH)/MeOH 9:1->MeOH).

Workup

  1. customThe crude product is purified via prep

Sources & evidence

ORD record
ord-21db28eb4aa241e28a6d5d23ed412aa1
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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