Dicyclohexylcarbodiimide → HCID 86291015, compound

HRID 718625Notes

Reaction equation

HRID 718625 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([C:34](O)=[O:35])=[N:32][CH:33]=4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[CH3:37][S:38]([NH2:41])(=[O:40])=[O:39].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:37][S:38]([NH:41][C:34](=[O:35])[C:31]1[CH:30]=[CH:29][C:28]([C:13]2[N:9]3[N:10]=[CH:11][CH:12]=[C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[C:8]3=[N:15][C:14]=2[C:16]#[C:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:33][N:32]=1)(=[O:40])=[O:39]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 117728384HCID 117728384, compound

Product 1

HCID 86291015HCID 86291015, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 40a (0.20 g, 0.42 mmol), methanesulfonamide (60 mg, 0.63 mmol), dicyclohexylcarbodiimide (90.0 mg, 0.44 mmol) and N,N-dimethylpyridin-4-amine (60.0 mg, 0.49 mmol) in DCM (5 mL) was stirred at rt overnight, then concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (MeOH/CH2Cl2 (1:20)) to obtain a solid, which was washed with methanol (10 mL) to yield the title compound 28 as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 9.50-9.41 (m, 1H), 8.62 (d, J=8.8 Hz, 1H), 8.41 (d, J=8.4 Hz, 1H), 8.30-8.27 (m, 2H), 8.03-7.99 (m, 2H), 7.82 (t, J=7.6 Hz, 1H), 7.73 (t, J=8.8 Hz, 1H), 7.65 (t, J=7.6 Hz, 1H), 6.51 (d, J=5.6 Hz, 1H), 4.08-3.97 (m, 4H), 3.99-3.80 (m, 4H), 2.96 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H23N7O4S: 554.2 (M+H). Found: 554.0.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash column chromatography on silica gel (MeOH/CH2Cl2 (1:20))
  4. customto obtain a solid, which
  5. washwas washed with methanol (10 mL)

Sources & evidence

ORD record
ord-77ab7152ac934bdba48195855e7b9468
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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