1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66550546, compound

HRID 1410121Notes

Reaction equation

HRID 1410121 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:15]3[N:31]=[CH:30][S:29][C:16]=3[N:17]=[C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=3)[N:19]=2)[CH:10]=[CH:11][CH:12]=1.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH:36][C:24](=[O:26])[C:23]1[CH:22]=[CH:21][C:20]([C:18]2[N:19]=[C:14]([NH:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([N:3]4[CH2:4][CH2:5][CH2:6][C@@H:2]4[CH3:1])[CH:8]=3)[C:15]3[N:31]=[CH:30][S:29][C:16]=3[N:17]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 68378984HCID 68378984, compound

Product 1

HCID 66550546HCID 66550546, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (80 mg, 0.19 mmol) and N1,N1-dimethylethane-1,2-diamine (18 mg, 0.2 mmol) in DCM (20 mL) was added 1-methyl-1H-indozole (92 mg, 1.12 mmol) and EDCI (217 mg, 1.12 mmol). The reaction mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was purified by column chromatography (DCM:MeOH=50:1) and product treated with conc. HCl to give (S)—N-(2-(dimethylamino)ethyl)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (22 mg, 24%) as HCl salt. 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.37 (s, 1H), 8.34 (s, 1H), 8.27 (s, 1H), 7.97-7.91 (m, 3H), 7.63-7.57 (m, 1H), 7.41 (d, 1H, J=8.1 Hz), 4.06-3.93 (m, 2H), 3.77-3.68 (m, 3H), 3.37-3.33 (m, 2H), 2.91 (s, 6H), 2.53-2.42 (m, 1H), 2.35-2.18 (m, 2H), 2.06-1.87 (m, 1H), 1.36 (d, 3H, J=6.6 Hz). LC-MS: 502 [M+H]+, tR=1.344 min. HPLC: 97.57% at 214 nm, 97.17% at 254 nm, tR=4.793 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (DCM:MeOH=50:1) and product
  3. additiontreated with conc. HCl

Sources & evidence

ORD record
ord-bb43b9d5dabd42439d19055988178a7b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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