Trifluoroacetic acid → HCID 178486738, compound

HRID 890970Notes

Reaction equation

C([O:5][C:6]([CH2:8][NH:9][C:10]([NH:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:40])=[N:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[C:6]([CH2:8][NH:9][C:10]([NH:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:40])=[N:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1)([OH:7])=[O:5]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178486735HCID 178486735, compound

Product 1

HCID 178486738HCID 178486738, compoundYield 65%

Procedure

Using an analogous procedure to that described in Example 4, N-(tert-butoxycarbonylmethyl)-N′-(2,6-dimethylphenyl)-N″-[6-methoxy-7-(2-pyrrolidin-1-ylethoxy)quinazolin-4-yl]guanidine was reacted with trifluoroacetic acid to give the title compound in 65% yield; NMR Spectrum: (DMSOd6, 100° C.) 1.78 (m, 4H), 2.32 (s, 6H), 2.67 (m, 4H), 2.94 (t, 2H), 3.85 (s, 3H), 4.09 (s, 2H), 4.28 (t, 2H), 7.1 (s, 1H), 7.19 (s, 3H), 7.74 (s, 1H), 8.48 (s, 1H), 10.8–11.7 (br s, 1H); Mass Spectrum: M+H+ 493.

Sources & evidence

ORD record: ord-c9a88c8c038b4777be33e546e75a4170
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001904B1

Reaction notes

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