1-Methoxy-2-propanol → HCID 66712580, compound

HRID 1262342Notes

Reaction equation

HRID 1262342 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]2)=[CH:11][CH:10]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH2:34][CH2:35][N:36]([CH2:39][C:40]([NH2:42])=[O:41])[CH2:37][CH:38]=2)=[CH:29][C:28]=1[O:43][CH3:44].C(N(CC)C(C)C)(C)C.COCC(O)C>>[CH3:44][O:43][C:28]1[CH:29]=[C:30]([C:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]([NH2:42])=[O:41])[CH2:35][CH:34]=2)[CH:31]=[CH:32][C:27]=1[NH:26][C:15]1[N:14]=[CH:13][C:12]2=[CH:11][CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:17]2[N:16]=1

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 66711269HCID 66711269, compoundHCID 86661678Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66712580HCID 66712580, compound

Conditions

Temperature
100 °C

Procedure

Into an 8-dram vial was added Trifluoro-methanesulfonic acid 7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (210.0 mg, 0.5625 mmol), 2-[4-(4-Amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetamide (180 mg, 0.69 mmol), N,N-Diisopropylethylamine (0.2940 mL, 1.688 mmol) and 1-Methoxy-2-propanol (2 mL, 20 mmol). The reaction mixture was heated at 100° C. overnight. After 18 h, the product, 2-(4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-3,6-dihydro-2H-pyridin-1-yl)-acetamide, was isolated after purification with reverse phase prep-hplc (gilson) as a brown solid (46 mg, 17%). LCMS (E/I+) 582 (M+H). NMR 1H (DMSO-d6)-10.04 (br s, 1H), 8.97 (s, 1H), 8.15 (d, 1H, J=8.43 Hz), 7.96 (s, 1H), 7.80 (d, 1H, J=7.44 Hz), 7.72 (s, 2H), 7.48 (m, 1H), 7.23 (d, 1H, J=8.4 Hz), 7.13 (m, 2H0, 7.0-6.93 (m, 3H), 6.17 (s, 1H0, 4.01-3.2 (series of s, m along with the water peak, 12H), 2.78 (m, 2H).

Sources & evidence

ORD record
ord-6cce4bcc356c4b729cb9bb826901bb0a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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