Diisopropyl Ether → HCID 117666826, compound

HRID 1526221Notes

Reaction equation

HRID 1526221 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[C:16]([CH3:33])[CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].Cl.Cl.[CH:36]1([NH2:42])[CH2:40][CH2:39][CH2:38][CH:37]1[NH2:41].C(N(C(C)C)CC)(C)C.C(OC(C)C)(C)C>O.CN1CCCC1=O>[NH2:41][C@@H:37]1[CH2:38][CH2:39][CH2:40][C@H:36]1[NH:42][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:21][CH2:22][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:24][CH2:25]3)=[C:16]([CH3:33])[CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 81531DiisopropylethylamineHCID 12988586cyclopentane-1,2-diamine dihydrochlorideHCID 88569548HCID 88569548, compound

Product 1

HCID 117666826HCID 117666826, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-chloro-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (200 mg), rac-(1R,2R)-cyclopentane-1,2-diamine dihydrochloride (230 mg), diisopropylethylamine (480 μL), and N-methylpyrrolidone (0.8 mL) was reacted in a microwave device at 150° C. for 2 hours. Water and diisopropyl ether were added thereto, and the precipitated solid was filtered to obtain rac-5-{[(1R,2R)-2-aminocyclopentyl]amino}-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (195 mg).

Workup

  1. customwas reacted in a microwave device at 150° C. for 2 hours
  2. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-b348146c29c64656a5d9247769dd2b85
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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