HCID 56646648, compound → HCID 178507130, compound

HRID 872354Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4([NH2:22])[CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[N:11]=[C:5]2[CH:4]=1>CN1CCCC1=O>[NH2:22][C:18]1([C:15]2[CH:14]=[CH:13][C:12]([C:10]3[N:11]=[C:5]4[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][N:6]4[C:9]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 1-[4-(7-methoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (408 mg, 1.10 mmol) in N-methylpyrrolidone (16 mL) at 100° C. was added Na2S (431 mg, 5.52 mmol, 5 equiv) in portions. The resulting mixture was heated at 160° C. for 30 min., cooled to room temperature, and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 8 min., gradient to 95% CH2Cl2: 5% MeOH over 5 min.; 95% CH2Cl2: 5% MeOH for 4 min., gradient to 80% CH2Cl2: 20% MeOH over 5 min., 80% CH2Cl2: 20% MeOH for 6.2 min., gradient to 75% CH2Cl2: 25% MeOH over 2.0 min., 75% CH2Cl2: 25% MeOH for 18.2 min.) to give 2-[4-(1-amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-ol (315 mg, 81%):

Workup

temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
customThe remaining material was purified
waitgradient to 95% CH2Cl2: 5% MeOH over 5 min.
wait95% CH2Cl2: 5% MeOH for 4 min.
waitgradient to 80% CH2Cl2: 20% MeOH over 5 min.
wait80% CH2Cl2: 20% MeOH for 6.2 min.
waitgradient to 75% CH2Cl2: 25% MeOH over 2.0 min.

Sources & evidence

ORD record: ord-d1e3c65ca5704c42b31714a163ba070f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Reaction notes

Loading…