tert-butyl (7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)acetate → tert-butyl [7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl]acetate

HRID 400725Notes

Reaction equation

HRID 400725 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]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[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]([CH2:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:23]2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 86657762tert-butyl (7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)acetateHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 76787421tert-butyl [7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinolin-2(1H)-yl]acetate

Procedure

The title compound was prepared following procedure described for Intermediate 1, step 2, but starting from tert-butyl (7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)acetate obtained in step 1 (3.32 g; 12.19 mmol) as a pale yellow powder (3.69 g; 99%). 1H NMR (DMSO-d6) δ 9.50 (s, 1H), 7.43-7.40 (m, 1H), 7.33 (m, 1H), 7.08 (d, J=8 Hz, 1H), 5.71 (bs, 2H), 3.68 (s, 2H), 3.30 (s, 2H), 2.78 (s, 4H), 1.43 (s, 9H). HPLC (Method A), Rt 1.82 min (Purity: 91.1%). LC/MS (Method B): 306.2 (M+H)+.

Sources & evidence

ORD record
ord-b7ac4fa23b65493a930b4025b439ac29
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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