Trifluoroacetic acid → HCID 86761889, compound

HRID 1262109Notes

Reaction equation

HRID 1262109 reaction equation
C(OC(=O)[NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]3[N:23]=[CH:22][C:21]4=[CH:24][CH:25]=[C:26]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([S:33](=[O:40])(=[O:39])[NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:28]=5)[N:20]4[N:19]=3)[CH:15]=2)[CH2:10][CH:9]1[OH:41])(C)(C)C.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>C(Cl)Cl>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[NH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]3[N:23]=[CH:22][C:21]4=[CH:24][CH:25]=[C:26]([C:27]5[CH:28]=[C:29]([S:33]([NH:34][C:35]([CH3:37])([CH3:36])[CH3:38])(=[O:39])=[O:40])[CH:30]=[CH:31][CH:32]=5)[N:20]4[N:19]=3)[CH:15]=2)[CH2:10][CH:9]1[OH:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66710994HCID 66710994, compound

Product 1

HCID 86761889HCID 86761889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled compound was prepared through an acid catalyzed deprotection using {6-[7-(3-tert-butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-hydroxy-indan-1-yl}-carbamic acid tert-butyl ester and trifluoroacetic acid in methylene chloride to provide as a light brown lyophilate. LCMS (E/I+) 493 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 9.64 (s, 1H), 9.05 (s, 1H), 8.50 (s, 1H), 8.45 (d, 1H, J=7.7 Hz), 8.38 (s, 3H), 7.88 (d, 1H, J=8.2 Hz), 7.83 (dd, 1H, J=7.8 Hz), 7.70 (t, 1H, J=7.8 Hz), 7.62 (broad s, 2H), 7.31 (d, 1H, J=8.3 Hz), 7.24 (d, 1H, J=4.7 Hz), 7.02 (d, 1H, J=4.7 Hz), 5.56 (s, 1H), 4.37 (s, 2H), 3.25 (dd, 1H, J=5.8, 16 Hz), 2.75 (d, 1H, J=16, 20 Hz), 1.11 (s, 9H).

Workup

  1. customto provide as a light brown lyophilate

Sources & evidence

ORD record
ord-a1edffd9f3e14316b6e64cfd04025d19
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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