Phosgene → {5-Chloro-4-[2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylcarbamoyl]-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl}acetic acid tert-butyl ester

HRID 558966Notes

Reaction equation

HRID 558966 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][N:8]1[C:14](=[O:15])C[CH2:12][N:11]([C:16](=[O:39])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([N:27]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]4[CH:34]=[CH:35][CH:36]=[CH:37][C:28]3=4)=[O:26])=[CH:21][C:20]=2[CH3:38])[C:10]2[C:40](F)=[CH:41][CH:42]=[CH:43][C:9]1=2)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)CN1C2C(=C([Cl:63])C=CC=2)NCC1=O)(C)(C)C.C(Cl)(Cl)=O.C(N(C(C)C)CC)(C)C.NCC1C=CC(C(N2CCCCC3C=CC=CC2=3)=O)=CC=1C>>[C:1]([O:5][C:6](=[O:45])[CH2:7][N:8]1[C:9]2[C:10](=[C:40]([Cl:63])[CH:41]=[CH:42][CH:43]=2)[N:11]([C:16](=[O:39])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([N:27]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]4[CH:34]=[CH:35][CH:36]=[CH:37][C:28]3=4)=[O:26])=[CH:21][C:20]=2[CH3:38])[CH2:12][C:14]1=[O:15])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 5

HCID 6371PhosgeneHCID 81531Diisopropylethylamine2×HCID 15896086(4-(Aminomethyl)-3-methylphenyl)(2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methanoneHCID 57470782(5-Chloro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetic acid tert-butyl esterHCID 59807185{6-Fluoro-5-[2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)-benzylcarbamoyl]-2-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl}acetic Acid Tert-Butyl Ester

Product 1

HCID 59807172{5-Chloro-4-[2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzylcarbamoyl]-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl}acetic acid tert-butyl ester

Procedure

Following the same procedure as described for 1D, (5-chloro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetic acid tert-butyl ester from Example 12E (450 mg, 1.5 mmol) was treated with phosgene (2.0 mmol) and diisopropylethylamine (2.0 mmol) followed by (4-aminomethyl-3-methylphenyl)-(2,3,4,5-tetrahydrobenzo[b]azepin-1-yl)methanone from Example F (450 mg, 1.5 mmol) and diisopropylethylamine (2.0 mmol). The product was purified by flash chromatography on silica (eluant pet.ether:EtOAC, 100:0 to 50:50) to give a pale red solid; yield 510 mg, 54%.

Workup

  1. customThe product was purified by flash chromatography on silica (eluant pet.ether:EtOAC, 100:0 to 50:50)
  2. customto give a pale red solid

Sources & evidence

ORD record
ord-bbdc6b8cdf5647608fa7d573b2f15f4f
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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