Triethylamine → (2-Methylcarbamoyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

HRID 720136Notes

Reaction equation

HRID 720136 reaction equation
Cl.CN.C[O:5][C:6]([C:8]1[NH:9][C:10]2[CH:11]=[C:12]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:13]=[C:14]3[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:16]=1[C:15]=23)=O.[CH2:30]([N:32](CC)CC)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[C:26]([O:25][C:23](=[O:24])[NH:22][C:12]1[CH:13]=[C:14]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:16]3=[C:8]([C:6](=[O:5])[NH:32][CH3:30])[NH:9][C:10]([CH:11]=1)=[C:15]23)([CH3:28])([CH3:27])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochloride2×HCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Product 1

HCID 136181651(2-Methylcarbamoyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterYield 29.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

Preparation of example 161 was carried out in a manner analogous to step 5 of Example 147, except that methylamine hydrochloride was substituted for methanol. Thus CO was bubbled through a mixture of Intermediate 147(d) from Example 147 (200 mg, 0.529 mmol), triethylamine (0.29 mL, 2.11 mmol), methylamine hydrochloride (71 mg, 1.06 mmol), and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (86 mg, 0.106 mmol). Reaction conditions, work up and silica gel chromatography (eluted with 46:4:25 dichloromethane:methanol:ethyl acetate) were also carried out in an analogous manner and afforded the title compound (55 mg, 0.154 mmol) in 29% yield.

Workup

  1. customPreparation of example 161
  2. customReaction conditions
  3. washsilica gel chromatography (eluted with 46:4:25 dichloromethane:methanol:ethyl acetate)

Sources & evidence

ORD record
ord-554a8e492d444a98bfb6cf1f3fff1deb
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

Loading…