Dimethylformamide → 1-[3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-((4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-3-yl)urea

HRID 1295434Notes

Reaction equation

HRID 1295434 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([C@@](O)([C@@H](O)[C@H](O)[C@H](O)CO)C(N)=O)=[CH:16][CH:15]=1.Cl.[OH:34][CH:35]1[O:43][C@H:42]([CH2:44][OH:45])[C@@H:40]([OH:41])[C@H:38]([OH:39])[C@H:36]1[NH2:37].C[N:47]([CH:49]=[O:50])C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([NH:47][C:49]([NH:37][CH:36]2[C@@H:38]([OH:39])[C@H:40]([OH:41])[C@@H:42]([CH2:44][OH:45])[O:43][CH:35]2[OH:34])=[O:50])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 69511913[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamide2×

Product 1

HCID 695113841-[3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-((4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-3-yl)urea

Procedure

254 mg (0.5 mmol) of 4-nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride (intermediate 1, Example 6) were initially charged in 7 ml of abs. DMF and admixed at 0° C. with a suspension of 119 mg (0.55 mol) of D-glucosamine hydrochloride in 5 ml of abs. DMF. A similar procedure to the method described in Example 6 afforded, after chromatography on silica gel, 87 mg of the title compound.

Workup

  1. customafforded

Sources & evidence

ORD record
ord-3f50a4a9a7f34c668c624d662019906e
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Reaction notes

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