1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58137246, compound

HRID 1424641Notes

Reaction equation

HRID 1424641 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:28])[NH:16][CH:17]3[CH:24]4[CH2:25][C:20]5(F)[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:30][C:31]([O:33]CC)=O.CC[N:38]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:38][C:31](=[O:33])[CH2:30][CH:7]1[C:6]2[C:29](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:9]2([CH2:10][CH2:11][N:12]([C:15]([NH:16][CH:17]3[CH:18]4[CH2:26][CH:22]5[CH2:21][CH:20]([CH2:25][CH:24]3[CH2:23]5)[CH2:19]4)=[O:28])[CH2:13][CH2:14]2)[CH2:8]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 70795071HCID 70795071, compound

Product 1

HCID 58137246HCID 58137246, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 1 (200 mg, 0.47 mmol) in CH2Cl2 (5 mL), EDCI (187 mg, 0.95 mmol), HOBt (128 mg, 0.95 mmol), DIEA (303 mg, 2.35 mmol) were added under NH3 at 0° C., and then stirred overnight. The solvent was removed under reduced pressure to give crude product, which was purified by preparative TLC to afford (±)-3-(2-amino-2-oxoethyl)-N-(2-adamantyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (110 mg, 56%). 1H NMR (CDCl3): δ=1.52-1.61 (m, 4H), 1.62-1.66 (m, 2H), 1.68-1.70 (m, 2H), 1.75-1.76 (m, 2H), 1.78-1.80 (m, 1H), 1.82-1.85 (m, 6H), 1.90-1.98 (m, 2H), 2.11-2.21 (m, 1H), 2.30-2.40 (m, 1H), 2.60-2.70 (m, 1H), 2.80-2.88 (m, 1H), 2.95-3.15 (m, 2H), 3.65-3.75 (m, 2H), 3.76-3.88 (m, 1H), 4.00 (s, 2H), 5.40-5.55 (d, 2H), 7.15-7.25 (m, 4H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-46448ce21aaa4bc7a08a88b340b92848
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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