Dimethylamine → HCID 131732815, compound

HRID 571361Notes

Reaction equation

HRID 571361 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:20][C@H:12]2[CH2:13][N:14]([CH2:16][C:17](O)=[O:18])[CH2:15][C@@:11]2([C:21]([N:23]2[CH2:32][CH2:31][C:30]3[N:29]=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[CH:26][C:25]=3[CH2:24]2)=[O:22])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH:38][CH3:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:20][C@H:12]2[CH2:13][N:14]([CH2:16][C:17]([N:38]([CH3:39])[CH3:37])=[O:18])[CH2:15][C@@:11]2([C:21]([N:23]2[CH2:32][CH2:31][C:30]3[N:29]=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[CH:26][C:25]=3[CH2:24]2)=[O:22])[CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89928727HCID 89928727, compound

Product 1

HCID 131732815HCID 131732815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution the product from Step A (37 mg, 0.072 mmol), dimethylamine (0.0433 mL, 0.0866 mmol, 2 M in THF), EDAC (18 mg, 0.0938 mmol), HOBt (19.51 mg, 0.144 mmol) and DIPEA (0.0252 mL, 0.144 mmol) in DMF (3 mL) was stirred at rt over the weekend. The reaction was quenched by addition of brine, extracted with EtOAc, dried over Na2SO4 and purified by CombiFlash (eluent: 8% methanol in DCM) to give the product as a yellowish gel. 1H-NMR (400 MHz, CDCl3): δ 1.29-1.43 (m, 9H), 1.75-2.09 (m, 4H), 2.20-2.35 (m, 1H), 2.55-2.71 (m, 3H), 2.86-3.00 (m, 4H), 3.05-3.22 (m, 6H), 3.60-3.93 (m, 2H), 4.25 (d, J=5.6 Hz, 1H), 4.59-4.92 (m, 3H), 7.70 (s, 1H), 8.70 (s, 1H); LC/MS: C26H36F3N5O4: m/z 540.3 (M+H).

Workup

  1. customThe reaction was quenched by addition of brine
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. custompurified by CombiFlash (eluent: 8% methanol in DCM)

Sources & evidence

ORD record
ord-7e739559d762425bb3dfa2a4d8ae9131
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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