N,N-Dimethylglycine → HCID 57860963, compound

HRID 1928816Notes

Reaction equation

HRID 1928816 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[CH:49]([NH:51][C:52]1[CH:61]=[CH:60][C:59]3[C:54](=[CH:55][CH:56]=[C:57]([NH2:62])[CH:58]=3)[N:53]=1)[CH2:48][CH2:47][CH2:46]2>ClCCl.CN(C)C=O.O>[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([NH:62][C:57]1[CH:58]=[C:59]2[C:54](=[CH:55][CH:56]=1)[N:53]=[C:52]([NH:51][CH:49]1[C:50]3[C:45](=[CH:44][CH:43]=[CH:42][C:41]=3[O:40][CH3:39])[CH2:46][CH2:47][CH2:48]1)[CH:61]=[CH:60]2)=[O:5]

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57860959Rac-n2-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-quinoline-2,6-diamine

Product 1

HCID 57860963HCID 57860963, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylglycine (49 mg, 0.48 mmol), N,N-diisopropyl ethyl amine (217 mg, 1.68 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (220 mg, 0.69 mmol) were dissolved in dichloromethane (6 mL) and dimethylformamide (1.5 mL). The reaction mixture was stirred at room temperature for 30 minutes. rac-N2-(8-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-quinoline-2,6-diamine (150 mg, 0.47 mmol) was added and stirred was continued overnight. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined organic phases were dried over sodium sulfate and evaporated. The crude product was purified by column chromatography (silica gel, dichloromethane/methanol 100:0→90:10). The title compound (147 mg, 77%) was obtained as a light brown solid; MS: m/e=405.5 (M+H+).

Workup

  1. stirringstirred
  2. waitwas continued overnight
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by column chromatography (silica gel, dichloromethane/methanol 100:0→90:10)

Sources & evidence

ORD record
ord-c2d72ed5172e4a05a975c22988ba767b
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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