1-Pyrrolidineethanamine → HCID 68697362, compound

HRID 1444620Notes

Reaction equation

HRID 1444620 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([OH:34])=[O:33])=[CH:12][C:13]=3[N:14]3[CH2:20][CH2:19][CH:18]([N:21]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])C)[C:17]4[CH:28]=[CH:29][CH:30]=[CH:31][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1(CCN)CC[CH2:37][CH2:36]1.[CH3:43]C#N>>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34][CH3:43])=[O:33])=[CH:12][C:13]=3[N:14]3[CH2:20][CH2:19][CH:18]([NH:21][CH2:23][CH2:24][N:25]4[CH2:26][CH2:37][CH2:36][CH2:27]4)[C:17]4[CH:28]=[CH:29][CH:30]=[CH:31][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 6342AcetonitrileHCID 11612307HCID 11612307, compound

Product 1

HCID 68697362HCID 68697362, compound

Procedure

A 0.03M solution of 5-bromo-13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (prepared as in Example 2) in MeCN was treated with (2-pyrrolidin-1-ylethyl)amine (5 eq) at 55° C. for 4 h; evaporation in vacuo to dryness gave crude methyl 13-cyclohexyl-5-[(2-pyrrolidin-1-ylethyl)amino]-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate. Hydrolysis of the foregoing methyl ester was done with IM aqueous KOH (6 eq) in dioxane (0.1M) at 60° C.; the reaction was complete in 2 h, and the title compound was obtained in 24% yield after RP-HPLC purification and lyophilisation (Conditions: Column: Waters X-TERRA MS C18, 10 micron, 19×150 mm; Gradient: A: H2O+0.1% TFA; B: MeCN+0.1% TFA; 75% A isocratic for 3 min, linear to 20% A in 12 min).

Workup

  1. customevaporation in vacuo to dryness

Sources & evidence

ORD record
ord-fa39d81a99de45688c7fdb5297ad12b3
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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