1-Methoxy-2-propanol → HCID 46851548, compound

HRID 1262272Notes

Reaction equation

HRID 1262272 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]([CH2:19][CH2:20][C:21]#[N:22])[CH:16]=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.[N:23]1([CH:29]2[CH2:35][CH2:34][C:33]3[CH:36]=[C:37]([NH2:40])[CH:38]=[CH:39][C:32]=3[CH2:31][CH2:30]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.COCC(O)C.C(N(CC)C(C)C)(C)C>>[N:23]1([CH:29]2[CH2:35][CH2:34][C:33]3[CH:36]=[C:37]([NH:40][C:4]4[N:9]=[CH:8][C:7]5=[CH:10][CH:11]=[C:12]([C:13]6[CH:14]=[C:15]([CH2:19][CH2:20][C:21]#[N:22])[CH:16]=[CH:17][CH:18]=6)[N:6]5[N:5]=4)[CH:38]=[CH:39][C:32]=3[CH2:31][CH2:30]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 574161367-morpholino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-amineHCID 66711876HCID 66711876, compound

Product 1

HCID 46851548HCID 46851548, compound

Procedure

Into a microwave vial, 3-[3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile (0.0964 g, 0.310 mmol), 7-Morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine (0.168 g, 0.683 mmol), 1-Methoxy-2-propanol (0.747 mL) and N,N-Diisopropylethylamine (0.119 mL) 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 10% methanol). The collected fractions afforded 3-{3-[2-(7-Morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-propionitrile as a yellow solid (35 mg, 23%). LCMS (E/I+) 493.20 (M+H). MP 184-186° C. NMR 1H (DMSO-d6)-9.34 (s, 1H), 8.97 (s, 1H), 8.18 (d, 1H, J=8.44 Hz), 8.02 (s, 1H), 7.56 (s, 1H), 7.97 (d, 2H, J=7.23 Hz), 7.35 (d, 1H, J=7.23 Hz), 7.18 (d, 1H, J=4.51 Hz), 7.05 (d, 1H, J=7.89), 6.95 (d, 1H, J=4.51 Hz), 3.54 (bs, 4H), 2.98 (t, 2H, J=7.32 Hz), 2.87 (t, 2H, J=7.04 Hz), 2.53-2.81 (m, 5H), 2.43-2.48 (m, 4H), 1.89-2.07 (m, 2H), 1.22-1.43 (m, 2H).

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-2927a25451914c72a496e8db378f4f4b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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