3-Fluorobenzyl bromide → (+/-)-{3-[{1-[3-(3-Fluorobenzyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl]-propyl}-(4-methylbenzoyl)-amino]-propyl}-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[CH:12]([C:15]1[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][N:17]2[N:16]=1)[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NCCCN(C(C1N(CC2C=CC(F)=CC=2)C(=O)C2=CC=CN2N=1)CC)C(=O)C1C=CC(C)=CC=1)(C)(C)C.[F:77][C:78]1[CH:79]=[C:80]([CH:83]=[CH:84][CH:85]=1)[CH2:81]Br>>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:15]1[N:20]([CH2:81][C:80]2[CH:83]=[CH:84][CH:85]=[C:78]([F:77])[CH:79]=2)[C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][N:17]2[N:16]=1)[CH2:13][CH3:14])[C:25](=[O:33])[C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=1)([CH3:2])([CH3:4])[CH3:3]Participants
Reactant 3
Product 1
Procedure
(±)-(3-{(4-Methylbenzoyl)-[1-(4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4] triazin-2-yl)-propyl]amino}propyl)carbamic acid tert-butyl ester (Example 3 A, 42 mg, 0.09 mmol) was converted to the title compound (7 mg, 13%) in a manner similar to the preparation of (±)-{3-[{1-[3-(4-fluorobenzyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl]-propyl}-(4-methylbenzoyl)-amino]-propyl}-carbamic acid tert-butyl ester, except that 3-fluorobenzyl bromide (22 mg, 0.12 mmol) was used instead of 4-fluorobenzyl bromide: 1H NMR (CDCl3) δ 7.45–6.96 (m, 10H), 6.62 (m, 1H), 5.95 (m, 1H), 5.86 (m, 1H), 4.90 (m, 1H), 3.86 (m, 1H), 3.33 (m, 2H), 2.71 (m, 2H), 2.39 (s, 3H), 2.05 (m, 1H), 1.85 (m, 1H), 1.60 (m, 1H), 1.40 (s, 9H), 1.05 (m, 1H), 0.72 (m, 3H).
Sources & evidence
- ORD record
- ord-9fc33f4153134b41a52217f85069f6ac
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030118B2
Reaction notes
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