1-Methoxy-2-propanol → HCID 66712293, compound

HRID 1262266Notes

Reaction equation

HRID 1262266 reaction equation
[CH2:1]([C:8]1[N:16]2[C:11]([CH:12]=[N:13][C:14](S(C)=O)=[N:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH2:1]([C:8]1[N:16]2[C:11]([CH:12]=[N:13][C:14]([NH:33][C:30]3[CH:29]=[CH:28][C:27]([N:24]4[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]4)=[CH:32][CH:31]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 66711700HCID 66711700, compound

Product 1

HCID 66712293HCID 66712293, compoundYield 42%

Procedure

Into a microwave vial, 7-Benzyl-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (0.120 g, 0.442 mmol), 4-(4-Methyl-piperazin-1-yl)-phenylamine (0.186 g, 0.973 mmol), N,N-Diisopropylethylamine (0.169 mL, 0.973 mmol), and 1-Methoxy-2-propanol (0.50 mL, 5.1 mmol) were added. The reaction was microwaved on 300 watts, 180° C. for 2 hours. The solvent was removed under vacuum. The reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN. The collected fractions were lyophilized to give a yellow solid (74 mg, 42%). LCMS (E/I+) 399.3 (M+H). NMR 1H (DMSO-d6)-9.74 (bs, 1H), 9.21 (s, 1H), 8.83 (s, 1H), 7.64 (d, 2H, J=8.09 Hz), 7.27-7.34 (m, 4H), 7.20 (bs, 1H), 6.96 (d, 2H, J=8.09 Hz), 6.78 (d, 1H, J=4.85 Hz), 6.60 (d, 1H, J=4.85 Hz), 4.27 (s, 2H), 3.74 (d, 2H, J=12.94 Hz), 3.52 (d, 2H, J=12.14 Hz), 3.09-3.24 (m, 2H), 2.77-2.97 (m, 5H).

Workup

  1. customThe reaction was microwaved on 300 watts, 180° C. for 2 hours
  2. customThe solvent was removed under vacuum
  3. customThe reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN

Sources & evidence

ORD record
ord-9f6f5ffa1a314ba29a98fdde6c247043
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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