Trifluoroacetic acid → HCID 57612646, compound

HRID 2074163Notes

Reaction equation

[C:1](O)(C(F)(F)F)=O.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[NH:20][C:21]1[N:29]=[C:28]2[C:24]([NH:25][C:26](=[O:36])[N:27]2[CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[C:23]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[N:22]=1>>[N:40]1[CH:39]=[CH:38][C:37]([C:23]2[N:22]=[C:21]([N:20]3[C:10]4[CH:11]=[C:12]([O:15][C:16]([F:19])([F:17])[F:18])[CH:13]=[CH:14][C:9]=4[N:8]=[CH:1]3)[N:29]=[C:28]3[C:24]=2[NH:25][C:26](=[O:36])[N:27]3[CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:42][CH:41]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67059556HCID 67059556, compound

Product 1

HCID 57612646HCID 57612646, compound

Procedure

Yellow oil. TFA salt. Synthesized from 2-(2-amino-5-(trifluoromethoxy)phenylamino)-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one following the general procedure for closing the benzimidazole ring. 1H NMR (300 MHz, CD3OD+CDCl3) δ, ppm: 9.30 (br s, 1H), 9.00-8.85 (br m, 1H), 8.67 (s, 1H), 8.20-8.10 (m, 2H), 7.84-7.67 (m, 1H), 7.40-7.22 (m, 2H), 4.76-4.72 (m, 1H), 4.26-4.13 (m, 2H), 3.62 (app t, 2H), 2.90-2.80 (m, 2H), 1.90 (br d, 2H); MS (EI) m/z 498.3 (MH)+.

Sources & evidence

ORD record: ord-51374e70a5044507a66be01aacd33d1a
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919490B2

Reaction notes

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