1-Bromo-1-methylcyclopropane → HCID 69591821, compound
Reaction equation
C(OC(=O)NCCCN(C(=O)C1C=CC(C)=CC=1)C(C1NC(=O)C2=CC=CN2N=1)CC)(C)(C)C.[C:35]([O:39][C:40](=[O:76])[NH:41][CH2:42][CH2:43][CH2:44][N:45]([CH:55]([C:58]1[N:63]([CH2:64][C:65]2C=CC(F)=[CH:67][CH:66]=2)[C:62](=[O:72])[C:61]2=[CH:73][CH:74]=[CH:75][N:60]2[N:59]=1)[CH2:56][CH3:57])[C:46](=[O:54])[C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1)([CH3:38])([CH3:37])[CH3:36].BrC1(C)CC1>>[C:35]([O:39][C:40](=[O:76])[NH:41][CH2:42][CH2:43][CH2:44][N:45]([CH:55]([C:58]1[N:63]([CH2:64][CH:65]2[CH2:66][CH2:67]2)[C:62](=[O:72])[C:61]2=[CH:73][CH:74]=[CH:75][N:60]2[N:59]=1)[CH2:56][CH3:57])[C:46](=[O:54])[C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1)([CH3:36])([CH3:37])[CH3:38]Participants
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 (8 mg, 17%) 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 bromo-methylcyclopropane (15 mg, 0.11 mmol) was used instead of 4-fluorobenzyl bromide: 1H NMR (CDCl3) δ 7.40–7.22 (m, 5H), 7.04 (m, 1H), 6.57 (m, 1H), 6.00 (m, 1H), 4.41 (m, 1H), 3.81 (m, 1H), 3.65 (m, 1H), 3.40–3.05 (m, 3H), 2.69 (m, 2H), 2.38 (s, 3H), 2.27 (m, 1H), 1.97 (m, 1H), 1.61 (m, 2H), 1.39 (s, 9H), 1.27 (m, 2H), 0.80–1.10 (m, 3H), 0.59 (m, 2H).
Sources & evidence
- ORD record
- ord-ca85517e099d43b69b1f172310876ff0
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030118B2
Reaction notes
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