Trifluoroacetic acid → HCID 86719396, compound

HRID 2175658Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[N:23]([CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[N:22]=[N:21][CH:20]=4)=[CH:13][CH:12]=3)=[C:9]([CH3:32])[N:8]([C@@H:33]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O>>[C:26]([O:25][CH2:24][N:23]1[C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]3[C:3]4[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=4[N:8]([C@@H:33]4[CH2:37][CH2:36][NH:35][CH2:34]4)[C:9]=3[CH3:32])=[CH:12][CH:13]=2)=[CH:20][N:21]=[N:22]1)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86719395HCID 86719395, compound

Product 1

HCID 86719396HCID 86719396, compoundYield 77.4%

Procedure

(R)-(5-((4-(4-Amino-6-methyl-7-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (84) (121 mg, quant. yield) was prepared by treating (R)-tert-butyl 3-(4-amino-6-methyl-5-(4-((1-(pivaloyloxymethyl)-1H-1,2,3-triazol-5-yl)methoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (83) (188 mg, 0.31 mmol) with TFA in a similar manner as described in Example 1. LC-MS (ESI): m/z (M+1) 505.0.

Sources & evidence

ORD record: ord-5a03ed0e02c44606b98c1c3efc8c26ee
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062058B2

Reaction notes

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