2-(3-(hydroxymethyl)phenyl)-N,N-dimethyl-4-morpholinopyrrolo[2,1-f][1,2,4]triazine-6-carboxamide → (3-(6-((Dimethylamino)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)phenyl)methanol

HRID 63797Notes

Reaction equation

HRID 63797 reaction equation
NC1C=CC(C2N=C(N3CCOCC3)C3=CC(CN(C)C)=CN3N=2)=CC=1.[OH:27][CH2:28][C:29]1[CH:30]=[C:31]([C:35]2[N:40]=[C:39]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[C:38]3=[CH:47][C:48]([C:50]([N:52]([CH3:54])[CH3:53])=O)=[CH:49][N:37]3[N:36]=2)[CH:32]=[CH:33][CH:34]=1>>[CH3:54][N:52]([CH2:50][C:48]1[CH:47]=[C:38]2[N:37]([CH:49]=1)[N:36]=[C:35]([C:31]1[CH:30]=[C:29]([CH2:28][OH:27])[CH:34]=[CH:33][CH:32]=1)[N:40]=[C:39]2[N:41]1[CH2:42][CH2:43][O:44][CH2:45][CH2:46]1)[CH3:53]

Participants

3

Reactant 2

HCID 1179878762-(3-(hydroxymethyl)phenyl)-N,N-dimethyl-4-morpholinopyrrolo[2,1-f][1,2,4]triazine-6-carboxamideHCID 117987912HCID 117987912, compound

Product 1

HCID 72549552(3-(6-((Dimethylamino)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)phenyl)methanol

Procedure

Compound I-24 was prepared by the method which was identical with that for preparing compound 13a, wherein compound 18 (70 mg, 0.184 mmol) was used as the starting material. White solid (100%). m.p. 163-165° C. 1H NMR (300 MHz, DMSO-d6): δ 8.20 (s, 1H), 8.11 (dt, J=2.4, 6.0 Hz, 1H), 7.99 (d, J=1.3 Hz, 1H), 7.45-7.41 (m, 2H), 7.15 (d, J=1.3 Hz, 1H), 5.27 (t, J=5.8 Hz, 1H), 4.57 (d, J=5.8 Hz, 2H), 4.07 (t, J=4.6 Hz, 4H), 3.95 (s, 2H), 3.80 (t, J=4.6 Hz, 4H), 2.44 (s, 6H). MS (EI) m/e (%): 367 (M+, 16).

Workup

  1. customCompound I-24 was prepared by the method which

Sources & evidence

ORD record
ord-b40772334d944a3cba201e87ee253112
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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