Piperidine → HCID 178483578, compound

HRID 2037025Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][CH:23]3[CH2:25][CH2:24]3)[N:19]3[N:26]=[CH:27][C:28]([CH:29]=O)=[C:18]3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].N1CCCCC1.[NH:37]1[CH2:43][C:41](=[O:42])[NH:40][C:38]1=[O:39]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][CH:23]3[CH2:25][CH2:24]3)[N:19]3[N:26]=[CH:27][C:28](/[CH:29]=[C:43]4/[C:41](=[O:42])[NH:40][C:38](=[O:39])[NH:37]/4)=[C:18]3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 85 °C

Procedure

To 5-(3-chloro-4-(3-(dimethylamino)propoxy)phenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (79 mg, 0.184 mmol) in EtOH (3 mL) was added piperidine (22 uL 0.221 mmol) followed by hydantoin (21 mg, 0.202 mmol). The reaction mixture was stirred at 85° C. for 6 h. The solvent was removed by rotary evaporation and the residue was diluted with 3 mL of water. The suspension was sonicated and the resulting solid was filtered off and washed with water followed by a 1:1 mixture of EtOH/water. The material was Dried under vacuum to provide 62 mg of (Z)-5-((5-(3-chloro-4-(3-(dimethylamino)propoxy)phenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione LCMS (ES): m/z 511 [M+1]+.

Workup

customThe solvent was removed by rotary evaporation
additionthe residue was diluted with 3 mL of water
customThe suspension was sonicated
filtrationthe resulting solid was filtered off
washwashed with water
additionfollowed by a 1:1 mixture of EtOH/water
customThe material was Dried under vacuum

Sources & evidence

ORD record: ord-fa44a0ffc50a49018f65e0bf40577ad3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

Loading…