2-Amino-4-methylthiazole → HCID 16752564, compound

HRID 240573Notes

Reaction equation

Cl.[N:2]1[CH:3]=[CH:4][N:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26](I)[CH:27]=5)[N:22]=[CH:21][N:20]=4)=[CH:14][C:13]=3[CH3:30])=[CH:7][C:6]=12.[CH3:31][C:32]1[N:33]=[C:34]([NH2:37])[S:35][CH:36]=1.CC([O-])(C)C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:2]1[CH:3]=[CH:4][N:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([NH:37][C:34]6[S:35][CH:36]=[C:32]([CH3:31])[N:33]=6)[CH:27]=5)[N:22]=[CH:21][N:20]=4)=[CH:14][C:13]=3[CH3:30])=[CH:7][C:6]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of N-(4-(imidazo[1,2-a]pyridin-7-yloxy)-3-methylphenyl)-6-iodoquinazolin-4-amine hydrochloride (0.20 g, 0.378 mmol) and 4-methylthiazol-2-amine (0.086 g, 0.755 mmol) and sodium 2-methylpropan-2-olate (0.145 g, 1.51 mmol), Xanthphos (0.016 g, 0.028 mmol), Pd2 dba3 (0.017 g, 0.018 mmol) in toluene (3.6 mL) was degassed and sealed. After heating to 100° C. for 16 hours, the mixture was diluted with water and ethyl acetate. The resulting solid was filtered to provide the product as brown solid. MS APCI (+) m/z 480 (M+1) detected; 1H NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 8.86 (s, 1H), 8.63 (s, 1H), 8.55 (d, 1H), 7.79 (m, 5H), 7.44 (s, 1H), 7.14 (d, 1H), 6.80 (dd, 1H), 6.55 (d, 1H), 2.50 (s, 3H), 2.21 (s, 3H).

Workup

customsealed
filtrationThe resulting solid was filtered

Sources & evidence

ORD record: ord-63f2cfc4d73e4fe58c13551f6fec1707
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648087B2

Reaction notes

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