Tetrahydrofuran → HCID 57737254, compound

HRID 1157646Notes

Reaction equation

HRID 1157646 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:27]=4)[N:20]=3)=[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.N([C@@H]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)C)=C=O.[CH2:49]1[CH2:53][O:52][CH2:51][CH2:50]1>>[CH3:37][N:35]([CH3:36])[CH2:34][CH2:33][O:32][C:28]1[CH:27]=[C:26]([NH:25][C:21]2[N:20]=[C:19]([C:18]3[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:51]([C:50]5([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[CH2:49][CH2:53]5)=[O:52])[CH:7]=[CH:6][CH:5]=4)=[N:9][N:10]4[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=34)[CH:24]=[CH:23][N:22]=2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 7018262(R)-(+)-1-Phenylethyl isocyanate2×HCID 57737217HCID 57737217, compound

Product 1

HCID 57737254HCID 57737254, compoundYield 44%

Procedure

4-[2-(3-Aminophenyl)-6-(methyloxy)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine (61 mg, 0.12 mmol) and [(1R)-1-isocyanatoethyl]benzene (34 mg, 0.23 mmol) were combined in THF (2 mL) and stirred for 2 h, after which time additional [(1R)-1-isocyanatoethyl]benzene (10 mg, 0.068 mmol) was added in portions until the reaction was complete by LC/MS. The mixture was absorbed onto silica get and purified by silica gel chromatography to afford the title compound as a yellow solid (34 mg, 44%). 1H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), 8.53 (d, J=5.9 Hz, 2H), 8.45 (d, J=9.9 Hz, 1H), 8.20 (d, J=5.5 Hz, 1H), 7.64 (s, 1H), 7.51 (s, 1H), 7.44 (d, J=7.4 Hz, 1H), 7.32-7.19 (m, 7H), 7.15-7.04 (m, 3H), 6.61 (d, J=8.5 Hz, 1H), 6.51 (d, J=8.1 Hz, 1H), 6.44 (d, J=5.2 Hz, 1H), 4.78 (t, J=7.4 Hz, 1H), 3.96 (t, J=5.5 Hz, 2H), 3.85 (s, 3H), 2.56 (t, J=5.7 Hz, 2H), 2.16 (s, 6H), 1.36 (d, J=7.1 Hz, 3H). ES-LC/MS m/z 643 [M+H]+.

Workup

  1. customThe mixture was absorbed onto silica
  2. customget
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2d02b5bd1b1548fea526f73bab4deae9
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…