Triethylamine → HCID 58550793, compound

HRID 2204285Notes

Reaction equation

HRID 2204285 reaction equation
C[CH2:2][N:3](CC)[CH2:4]C.[CH3:8][N:9]1[C:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[O:20][C:21]3([CH2:26][CH2:25][N:24]([C:27]([C:29]4[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=4[C:31]([OH:33])=O)=[O:28])[CH2:23][CH2:22]3)[C:12]=2[CH:11]=[N:10]1.Cl.CNC.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:2][N:3]([CH3:4])[C:31](=[O:33])[C:30]1[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=1[C:27]([N:24]1[CH2:25][CH2:26][C:21]2([C:12]3[CH:11]=[N:10][N:9]([CH3:8])[C:13]=3[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[O:20]2)[CH2:22][CH2:23]1)=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58551116HCID 58551116, compound

Product 1

HCID 58550793HCID 58550793, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Et3N (170 μL, 1.2 mmol) was added to a mixture of 2-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzoic acid (100 mg, 0.25 mmol), N-methylmethanamine hydrochloride (30 mg, 0.37 mmol), EDCI (48 mg, 0.25 mmol), and CH2Cl2 (1.5 mL) at ambient temperature. The mixture was allowed to stir for 16 h before it was diluted with CH2Cl2 and was washed with 1N HCl. The layers were separated and the organic layer was washed with 1N NaOH, and then brine before it was dried over sodium sulfate and was concentrated in vacuo to give N,N-dimethyl-2-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzamide (38 mg) as a white solid. ESI-MS m/z calc. 430.2, found 431.3 (M+1)+; Retention time: 2.24 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.56 (d, J=7.7 Hz, 1H), 7.45-7.37 (m, 3H), 7.46-7.22 (m, 2H), 7.30-7.21 (m, 1H), 7.13-7.00 (m, 2H), 4.52 (d, J=13.5 Hz, 1H), 4.19 (s, 3H), 3.74-3.51 (m, 2H), 3.31 (t, J=11.9 Hz, 1H), 3.09 (s, 3H), 2.94 (s, 3H), 2.24-2.02 (m, J=13.9 Hz, 2H), 2.02-1.76 (m, 2H).

Workup

  1. washwas washed with 1N HCl
  2. customThe layers were separated
  3. washthe organic layer was washed with 1N NaOH
  4. dry with materialbrine before it was dried over sodium sulfate
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-a8577cfd0a5e48c09a845b67fd1dc389
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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