N,N-Dimethyl-1,3-propanediamine → tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[3-(dimethylamino)propyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8a H,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate

HRID 2280215Notes

Reaction equation

HRID 2280215 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:43])[C:9]1[S:21][C:20]2[CH2:19][C@@H:18]3[C@H:13]([CH2:14][C@@H:15]([C:23]([N:25]([CH2:38][CH2:39][CH3:40])[C:26](=[O:37])OC4C=CC([N+]([O-])=O)=CC=4)=[O:24])[CH2:16][N:17]3[CH3:22])[CH2:12][C:11]=2[C:10]=1[C:41]#[N:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:44][CH2:45][CH2:46][CH2:47][N:48]([CH3:50])[CH3:49]>O1CCCC1>[C:41]([C:10]1[C:11]2[CH2:12][C@@H:13]3[C@@H:18]([CH2:19][C:20]=2[S:21][C:9]=1[N:8]([CH3:43])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[N:17]([CH3:22])[CH2:16][C@H:15]([C:23]([N:25]([C:26](=[O:37])[NH:44][CH2:45][CH2:46][CH2:47][N:48]([CH3:50])[CH3:49])[CH2:38][CH2:39][CH3:40])=[O:24])[CH2:14]3)#[N:42]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 867310284-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-N-propylcarbamate

Product 1

HCID 86731032tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[3-(dimethylamino)propyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8a H,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]-quinolin-6-yl]carbonyl}-N-propylcarbamate (200 mg) and tetrahydrofuran (3 mL) was added (3-aminopropyl)dimethylamine (0.082 mL) while stirring at room temperature, and then stirred at the same temperature for 22 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution) to give tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[3-(dimethylamino)propyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno-[3,2-g]quinolin-2-yl]-N-methylcarbamate (118 mg).

Workup

  1. stirringstirred at the same temperature for 22 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-e99862b29eef43c5bbd00d583f605607
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

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