tert-butyl 7-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-butyl 7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 400723Notes

Reaction equation

HRID 400723 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:13]=[CH:12][C:8]2NC=N[C:7]=2[CH:6]=1)[NH2:4].C(C1C=C2C([CH2:20][CH2:21][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]2)=CC=1)#N>>[NH2:4][C:3](=[N:2][OH:1])[C:5]1[CH:6]=[C:7]2[C:8]([CH2:20][CH2:21][N:22]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:23]2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 19381944tert-butyl 7-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 76787423tert-butyl 7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 80%

Procedure

The title compound was prepared following procedure described for Intermediate 1, step 2, but starting from tert-butyl 7-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate obtained in step 1 (1.50 g; 5.81 mmol). The solvent was evaporated in vacuo and further freeze dried to give the title compound as an off-white solid (1.35 g, 80%). 1H NMR (DMSO-d6) δ 9.54 (s, 1H), 7.46 (m, 2H), 7.14 (d, J=8 Hz, 1H), 5.74 (bs, 2H), 4.49 (s, 2H), 3.54 (t, J=5.9 Hz, 2H), 2.76 (t, J=5.9 Hz, 2H), 1.49 (s, 9H). HPLC (Method A), Rt 2.40 min (Purity: 99.4%). LC/MS (Method B): 292.2 (M+H)+.

Workup

  1. customThe title compound was prepared following procedure
  2. customThe solvent was evaporated in vacuo and further freeze
  3. customdried

Sources & evidence

ORD record
ord-8702883b54a1410d8cbc1138713d8eba
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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