Trifluoroacetic acid → HCID 67014877, compound

HRID 271292Notes

Reaction equation

HRID 271292 reaction equation
C([O:5][C@@H:6]([C@@H:8]1[CH2:12][O:11][C:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][N:18]=[C:17]3[NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[S:34][CH:35]=[CH:36][N:37]=3)=[C:27]([Cl:38])[CH:26]=2)=[N:9]1)[CH3:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:38][C:27]1[CH:26]=[C:25]([NH:24][C:17]2[C:16]3[C:21](=[CH:22][CH:23]=[C:14]([NH:13][C:10]4[O:11][CH2:12][C@@H:8]([C@H:6]([OH:5])[CH3:7])[N:9]=4)[CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH2:32][C:33]1[S:34][CH:35]=[CH:36][N:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68943067HCID 68943067, compound

Product 1

HCID 67014877HCID 67014877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-((S)-2-(4-(3-chloro-4-(thiazol-2-ylmethoxy)phenylamino)quinazolin-6-ylamino)-4,5-dihydrooxazol-4-yl)ethanol is prepared from (1R, 4S)-N6-[4-(1-tert-butoxyethyl)-4,5-dihydrooxazol-2-yl]-N4-[3-chloro-4-(thiazol-2-ylmethoxy)-phenyl]-quinazoline-4,6-diamine by standard deprotection methods using TFA in methylene chloride. MS ESI (+) m/z 497, 499 (M+1, Cl pattern) detected; 1H NMR (400 mHz, DMSO-D6) δ 9.53 (s, 1H), 8.47 (s, 1H), 8.08 (d, 1H), 7.87 (d, 1H), 7.80 (d, 1H), 7.76 (dd, 1H), 7.66 (m, 2H), 7.33 (d, 1H), 5.55 (s, 2H), 4.81 (m, 1H), 4.37 (m, 1H), 4.20 (m, 1H), 3.83 (m, 1H), 3.63 (m, 1H), 1.06 (d, 3H).

Sources & evidence

ORD record
ord-591380dc88ea487eb4adc8bb4db7dff5
Source dataset
uspto-grants-2008_11
Patent number
US07452895B2

Reaction notes

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