1-Methoxy-2-propanol → HCID 66712400, compound

HRID 1262281Notes

Reaction equation

HRID 1262281 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[C:15]([CH:24]=[CH:25][CH:26]=3)[CH2:16][NH:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1.COCC(O)C.C(N(CC)C(C)C)(C)C>>[CH3:23][S:20]([CH2:19][CH2:18][NH:17][CH2:16][C:15]1[CH:14]=[C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:40][C:37]4[CH:36]=[CH:35][C:34]([N:31]5[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]5)=[CH:39][CH:38]=4)=[N:5]3)=[CH:10][CH:11]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 66712452HCID 66712452, compound

Product 1

HCID 66712400HCID 66712400, compound

Procedure

Into a microwave vial, [3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-(2-methanesulfonyl-ethyl)-amine (0.100 g, 0.000255 mol), 4-(4-Methyl-piperazin-1-yl)-phenylamine (0.214 g, 0.00112 mol), 1-Methoxy-2-propanol (0.613 mL) and N,N-Diisopropylethylamine (0.133 mL, 0.000764 mol) were added. The reaction was microwaved on 300 watts, 170° C. for 50 minutes. The solvent was removed under vacuum. The desired product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 15% methanol). The collected fractions afforded (7-{3-[(2-Methanesulfonyl-ethylamino)-methyl]-phenyl}-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine a yellow solid (41 mg, 31%). LCMS (E/I+) 520.16 (M+H). NMR 1H (DMSO-d6)-9.76 (ns, 1H), 9.37 (s, 1H), 9.20 (bs, 2H), 8.99 (s, 1H), 8.42 (d, 2H, J=7.45 Hz), 8.16 (s, 1H), 7.61-7.72 (m, 3H), 7.51 (d, 1H, J=7.45 Hz), 7.15 (d, 1H, J=4.47 Hz), 6.91-7.04 (m, 4H), 4.31 (s, 2H), 3.76 (d, 2H, J=12.66 Hz), 3.34-3.63 (m, 6H0, 3.08-3.24 (m, 5H), 2.82-3.00 (m, 5H).

Workup

  1. customThe reaction was microwaved on 300 watts, 170° C. for 50 minutes
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8ff1d535268749b0b8ff3a47c72e3e4b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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