(3R)-(+)-3-(Dimethylamino)pyrrolidine → HCID 59553338, compound

HRID 1171292Notes

Reaction equation

HRID 1171292 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH3:38][N:39]([CH3:45])[C@@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1>>[CH3:38][N:39]([CH3:45])[C@@H:40]1[CH2:44][CH2:43][N:42]([C:21]2[N:20]=[C:19]([O:18][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:29]=[C:30]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)[CH:31]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)[CH:24]=[CH:23][N:22]=2)[CH2:41]1

Participants

3

Reactant 2

HCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553338HCID 59553338, compound

Procedure

Compound is prepared from 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide and (R)—N,N-dimethylpyrrolidin-3-amine according to conditions described in general procedure C. Mp: 115-117° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.70-2.10 (m, 2 H), 2.13 (s, 6 H), 2.68-3.10 (m, 5 H), 3.25 (t, J=4.4 Hz, 4 H), 3.74 (t, J=4.8 Hz, 4 H), 6.15 (bd, 1 H), 7.04 (d, J=12.0 Hz, 1 H), 7.24 (d, J=8.4 Hz, 1 H), 7.40-7.61 (m, 5 H), 7.84 (d, J=8.0 Hz, 1 H), 7.98 (d, J=8.4 Hz, 1 H), 8.22 (d, J=5.5 Hz, 1 H), 10.45 (s, 1 H).

Sources & evidence

ORD record
ord-e04616edaf2a47c199ca2e489bafc8dd
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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