Trifluoroacetic acid → HCID 178461300, compound

HRID 2194573Notes

Reaction equation

HRID 2194573 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]=[C:13]([O:15][CH2:16][CH:17]3[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)[C:12]([C:28]3[CH:33]=[CH:32][C:31]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[CH:30][CH:29]=3)=[CH:11][N:10]=2)[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>>[NH:19]1[CH2:18][CH:17]([CH2:16][O:15][C:13]2[C:12]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:35][CH2:36][O:37][CH2:38][CH2:39]4)=[CH:32][CH:33]=3)=[CH:11][N:10]=[C:9]([NH:8][C@H:5]3[CH2:6][CH2:7][C@@H:2]([CH3:1])[CH2:3][CH2:4]3)[N:14]=2)[CH2:20]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452153HCID 178452153, compound

Product 1

HCID 178461300HCID 178461300, compound

Procedure

Using the procedure of Example 1 Step 4, tert-butyl 3-((2-(cis-4-methylcyclohexylamino)-5-(4-morpholinophenyl)pyrimidin-4-yloxy)methyl)azetidine-1-carboxylate was deprotected by TFA to provide the title compound at quantitative yield. 1H NMR (CDCl3, 400 MHz) 8.02 (s, 1H), 7.32 (d, 2H), 6.87 (d, 2H), 5.24 (sb, 1H), 4.42 (d, 2H), 4.05 (m, 1H), 3.82-3.80 (m, 4H), 3.65 (m, 2H), 3.50 (m, 2H), 3.14-3.11 (m, 4H), 3.05 (bs 1H), 3.03-2.97 (m, 1H), 1.79-1.48 (m, 6H), 1.23-1.18 (m, 3H), 0.88 (d, 3H); MS (ESI) m/z: Calc: 437.3 (M+). Found. 438.3 (M+1).

Sources & evidence

ORD record
ord-637f2c6117b6451ca7c2dd59b45bb2e7
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

Loading…