3-(Bromomethyl)-1H-indazole, N1-BOC protected → HCID 69314041, compound

HRID 900101Notes

Reaction equation

HRID 900101 reaction equation
[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[CH2:15][C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2].[C:35]([O:39][C:40]([N:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([CH2:51]Br)=[N:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:39][C:40]([N:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]([CH2:51][CH:15]2[C:14]3[N:10]([C:11]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:12][N:13]=3)[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[N:7]([CH2:6][C:5](=[O:28])[N:4]([CH:1]([CH3:3])[CH3:2])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16]2=[O:17])=[N:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]

Participants

3

Reactant 2

HCID 108049513-(Bromomethyl)-1H-indazole, N1-BOC protectedHCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

Product 1

HCID 69314041HCID 69314041, compoundYield 63%

Procedure

Following the procedure described for Example 3(A), Step A, N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide (Preparation 7(A)) (411.7 mg, 0.9118 mmol) was alkylated with 3-bromomethyl-indazole-1-carboxylic acid tert-butyl ester (309 mg, 0.993 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (EtOAc to 5% MeOH in EtOAc) provided 391.9 mg of 3-{6-[(isopropyl-phenyl-carbamoyl)-methyl]-5-oxo-1-phenyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulen-4-ylmethyl}-indazole-1-carboxylic acid tert-butyl ester. 1H NMR (CD3OD) δ 7.99 (m, 2H), 7.22-7.66 (m, 15H), 7.01 (dd, 1H), 4.53-4.81 (m, 3H), 3.88-4.21 (m, 3H), 1.65 (m, 9H), 0.94 (m, 6H).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (EtOAc to 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-4011ebaceaba46f38057409828678727
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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