Acetonitrile → HCID 10022738, compound

HRID 599162Notes

Reaction equation

HRID 599162 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:29][CH3:30])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23](C(=O)C)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:8]=1.CC#N.CC1N=C(NC)SC=1C1C=CN=C(NC2C=C(C=CC=2)CNC(=O)C)N=1.[N+]([O-])(O)=O.N(C1C=C(C=CC=1)CNC(=O)C)C(N)=N>Cl>[CH3:1][C:2]1[N:3]=[C:4]([NH:29][CH3:30])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)=[CH:18][CH:19]=2)[N:8]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 10320107HCID 10320107, compoundHCID 10361685HCID 10361685, compoundHCID 178474544HCID 178474544, compound

Product 1

HCID 10022738HCID 10022738, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

By hydrolysis of 1-(4-{4-[4-(4-Methyl-2-methylamino-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone in 2 M aq HCl. Yellow solid. Anal. RP-HPLC: tR=8.8 min (10-70% MeCN, purity >95%). 1H-NMR (DMSO-d6) δ: 2.45 (3, 3H, CH3), 2.83 (t, 4H, J=5.9 Hz, CH2), 2.85 (d, 3H, J=4.9 Hz, CH2), 2.95 (t, 4H, J=4.9 Hz, CH2), 6.81 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 6.85 (d, 2H, J=9.3 Hz, Ph-H), 7.58 (d, 2H, J=8.8 Hz, Ph-H), 7.99 (m, 1H, NH), 8.26 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.14 (brs, 1H). N-{3-[4-(4-Methyl-2-methylamino-thiazol-5-yl)-pyrimidin-2-ylamino]-benzyl}-acetamide [63]. By condensation of 3-dimethylamino-1-(2-methylamino-4-methyl-thiazol-5-yl)-propenone and N-(3-guanidino-benzyl)-acetamide nitrate. Yellow solid. Mp 253-255° C. Anal. RP-HPLC: tR=11.3 min (10-70% MeCN, purity >95%): 1H NMR (DMSO): δ 1.86 (s, 3H, CH3), 2.46 (s, 3H, CH3), 2.85 (s, 2H, CH2), 3.09 (s, 3H, CH3), 6.82 (d, 1H, J=8.0 Hz, ph-H), 6.88 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.2 (t, 1H, J=8.0 Hz, Ph-H), 7.60 (d, 1H, J=8.0 Hz, Ph-H), 7.73 (s, 1H, Ph-H), and 8.32 (d, 1H, J=5.5 Hz, pyrimidinyl-H). MS (ESI+) m/z 391.55 [M+Na] (C18H20N6OSNa requires 391.46).

Sources & evidence

ORD record
ord-0dd720e18c4443a2a32133e028a97cbf
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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