Trifluoroacetic acid → (R)-1-{7-Methoxy-8-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-propan-2-ol

HRID 1262159Notes

Reaction equation

HRID 1262159 reaction equation
[NH2:1][C:2]1[C:16]([O:17][CH3:18])=[CH:15][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C@H:12]([OH:14])[CH3:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.CS([C:22]1[N:27]=[CH:26][C:25]2=[CH:28][CH:29]=[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[N:24]2[N:23]=1)=O.C(O)(C(F)(F)F)=O>>[CH3:18][O:17][C:16]1[C:2]([NH:1][C:22]2[N:27]=[CH:26][C:25]3=[CH:28][CH:29]=[C:30]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[O:37][CH3:38])[N:24]3[N:23]=2)=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([CH2:11][C@H:12]([OH:14])[CH3:13])[CH2:7][CH2:6][C:5]=2[CH:15]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 66711392(R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol

Product 1

HCID 66711706(R)-1-{7-Methoxy-8-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-propan-2-ol

Procedure

Following a procedure analogous to 251c, (R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol (0.139 g, 0.557 mmol) and 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (64 mg, 0.22 mol) were converted to the title compounds (22.66 mgs) as a TFA salt. H-NMR (CDCl3) δ 9.30 (broad s, 1H, TFA), 8.96 (s, 1H), 7.97 (s, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.61 (s, 1H), 7.50-7.45 (m, 1H), 7.26-7.21 (m, 1H), 7.14-7.09 (m, 1H), 6.99-6.93 (m, 2H), 6.93 (s, 1H), 4.22-4.12 (m, 1H), 3.86 (s, 3H), 3.78 (s, 3H), 3.69-3.60 (m, 2H), 3.29-2.93 (complex series of m, 8H), 1.16 (d, J=6.0 Hz, 3H); LC/MS (ESI+): 474.6 (M+H).

Sources & evidence

ORD record
ord-3e2acd2644564fa0b1617f0033edc7d3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…