Methanesulfonamide → HCID 86703793, compound

HRID 1849914Notes

Reaction equation

HRID 1849914 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][C:16]([F:21])([F:20])[CH2:15]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:22][S:23]([NH2:26])(=[O:25])=[O:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][C:16]([F:21])([F:20])[CH2:15]2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:26][S:23]([CH3:22])(=[O:25])=[O:24])=[O:8]

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703791HCID 86703791, compound

Product 1

HCID 86703793HCID 86703793, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from step 3, methanesulfonamide (32 mg), HBTU (86 mg), and DIPEA (0.18 mL) in dichloromethane (1.7 mL) was stirred at rt for 16 hr. Diluted with EtOAc, the contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (2×) and brine, and dried (Na2SO4). The crude was purified with HPLC. LCMS (Method D): RT=5.35 min, m/z: 400.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 12.08 (s, 1H), 7.78 (d, J=7.7 Hz, 1H), 7.14 (d, J=12.3 Hz, 1H), 4.13-3.98 (m, 2H), 3.13 (s, 3H), 2.18 (s, 1H), 2.04 (s, 2H), 1.90-1.56 (m, 4H), 1.55-1.39 (m, 1H), 1.19 (m, 1H).

Workup

  1. washthe contents were washed with 1:4 mixture of 1M HCl and 1M NaH2PO4 (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. customThe crude was purified with HPLC

Sources & evidence

ORD record
ord-4a44efe4ea45424ea31349e090911e47
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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