HCID 18463943, compound → HCID 18463943, compound

HRID 2231081Notes

Reaction equation

HRID 2231081 reaction equation
C([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH2:17][N:18]2[C:24](=[O:25])[CH:23]([NH:26][C:27]([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)=[O:28])[CH2:22][CH2:21][C:20](=[O:39])[N:19]2[CH2:40][CH2:41][CH3:42])=[O:16])[CH2:12][C:11](=[O:43])[O:10]1)C1C=CC=CC=1.[CH2:44]([N:51]1[C:57](=[O:58])[CH2:56][CH2:55][CH:54]([NH:59][C:60]([C:62]2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)[CH:65]=[CH:64][N:63]=2)=[O:61])[C:53](=[O:72])[N:52]1[CH2:73][C:74]([NH:76][CH:77]([CH:82]=[O:83])[CH2:78][C:79]([OH:81])=[O:80])=[O:75])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[C:29]1([C:27]([NH:26][CH:23]2[C:24](=[O:25])[N:18]([CH2:17][C:15]([NH:14][CH:13]([CH:9]=[O:8])[CH2:12][C:11]([OH:43])=[O:10])=[O:16])[N:19]([CH2:40][CH2:41][CH3:42])[C:20](=[O:39])[CH2:21][CH2:22]2)=[O:28])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][N:30]=1.[CH2:44]([N:51]1[C:57](=[O:58])[CH2:56][CH2:55][CH:54]([NH:59][C:60]([C:62]2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)[CH:65]=[CH:64][N:63]=2)=[O:61])[C:53](=[O:72])[N:52]1[CH2:73][C:74]([NH:76][CH:77]([CH:82]=[O:83])[CH2:78][C:79]([OH:81])=[O:80])=[O:75])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

4

Reactant 2

HCID 18463943HCID 18463943, compoundHCID 22956506HCID 22956506, compound

Product 2

HCID 18463940HCID 18463940, compoundHCID 18463943HCID 18463943, compoundYield 35%

Procedure

3-(2-(6-[(Isoquinoline-1-carbonyl)-amino]-3,7-dioxo-2-propyl-[1,2]diazepan-1-yl)-acetylamino)-4-oxo-butyric acid (11b) was prepared from isoquinoline-1-carboxylic acid {2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-1-propyl-[1,2]diazepan-4-yl}-amide (10b, diastereomers) (95 mg, 0.16 mmol) by the method used to prepare 11a to afford 28 mg (35% yield) of the title compound. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 mL/3 drops) δ 0.90-1.00 (t, 3H), 1.65-1.80 (m, 2H), 2.10-2.28 (m, 1H), 2.32-2.40 (m, 1H), 2.47-2.80 (m, 3H), 3.05-3.18 (m, 1H), 3.30-3.51 (m, 2H), 4.00-4.55 (m, 3H), 5.10-5.20 (m, 1H), 7.75-8.05 (m, 4H), 8.49 (s, 1H), 8.90-9.00 (m, 1H). Analytical HPLC: 6.26 min. LC-MS (ES+): m/e=498 (M+H+).

Sources & evidence

ORD record
ord-2930224274364e79b63ebd803621cda7
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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