1H-indazol-7-amine → N2,N4-bis(7-indazolyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine

HRID 71377

Reaction equation

HRID 71377 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][N:21]=[CH:20]2>>[NH:22]1[C:23]2[C:19](=[CH:18][CH:17]=[CH:16][C:15]=2[NH:14][C:2]2[N:7]=[C:6]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:23]=3[NH:22][N:21]=[CH:20]4)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=2)[CH:20]=[N:21]1

Participants

3

Reactant 2

HCID 889011H-indazol-7-amineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylate

Product 1

HCID 22060714N2,N4-bis(7-indazolyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine

Procedure

In like manner to N2,N4-bis(3-hydroxyphenyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine, 2,4-dichloro-5-ethoxycarbonylpyrimidine and 7-aminoindazole were reacted to yield N2,N4-bis(7-indazolyl)-5-ethoxycarbonyl-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 8.70 (s, 1H), 7.54 (d, 2H J=8.4 Hz), 7.37 (m, 6H), 4.3 (q, 2H, J=7.0 Hz), 1.33 (3H, J=7 Hz); LCMS: ret. time 23.61 min.; purity: 94%; MS (m/e): 415 (MH+).

Sources & evidence

ORD record
ord-5983169fbee1400f919f7a16c0379cf0
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

Loading…