N,N-Dimethylglycine → HCID 59640544, compound

HRID 2250120Notes

Reaction equation

HRID 2250120 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][NH:19][CH2:20]3)=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[CH3:55][N:56]([CH3:61])[CH2:57][C:58](O)=[O:59].C(O)C(N)(CO)CO>>[CH3:55][N:56]([CH3:61])[CH2:57][C:58]([N:19]1[CH2:18][CH2:17][C:16]2[C:21](=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:14][CH:15]=2)[CH2:20]1)=[O:59]

Participants

7

Reactant 6

HCID 673N,N-Dimethylglycine2×HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-Hydroxybenzotriazole2×HCID 69311509HCID 69311509, compound

Product 1

HCID 59640544HCID 59640544, compound

Procedure

2-Dimethylamino-1-[7-(3-piperidin-1-yl-propoxy)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone is prepared from 7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (175 mg, 0.5 mmol), PS-DCC (800 mg, 1.1 mmol), HOBt (80 mg, 0.77 mmol), NEt3 (0.21 mL, 1.5 mmol) and N,N-dimethylglycine (1.1 mL, 15 mmol) via a procedure substantially analogous to Procedure E except that PS-trisamine resin beads (700 mg, 2.6 mmol) is used in the work up to scavenge the excess HOBt and N,N-dimethylglycine. The free base product (35 mg, 19% yld) is isolated as an oil. MS(ES+)360.5(M+H)+.

Workup

  1. customThe free base product (35 mg, 19% yld) is isolated as an oil

Sources & evidence

ORD record
ord-d50d783bad984b5cbe5a6b0d13e3ac86
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

Loading…