Methanesulfonyl chloride → Methanesulfonic acid 1-(6-{(1R,4S)-4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]-1,2,3,4-tetrahydro-naphthalen-1-yloxy}-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-ylmethyl ester

HRID 2200040Notes

Reaction equation

HRID 2200040 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:10]1[CH:11]=[C:12]([NH:16][C:17]([NH:19][C@@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@H:23]([O:30][C:31]3[CH:32]=[CH:33][C:34]4[N:35]([C:37]([N:40]5[CH2:45][CH2:44][CH:43]([CH2:46][OH:47])[CH2:42][CH2:41]5)=[N:38][N:39]=4)[CH:36]=3)[CH2:22][CH2:21]2)=[O:18])[N:13]([CH3:15])[N:14]=1)([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:6]([C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:18])[NH:19][C@@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@H:23]([O:30][C:31]3[CH:32]=[CH:33][C:34]4[N:35]([C:37]([N:40]5[CH2:45][CH2:44][CH:43]([CH2:46][O:47][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:42][CH2:41]5)=[N:38][N:39]=4)[CH:36]=3)[CH2:22][CH2:21]2)[N:13]([CH3:15])[N:14]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1177290431-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-[3-(4-hydroxymethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea

Product 1

HCID 117728708Methanesulfonic acid 1-(6-{(1R,4S)-4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]-1,2,3,4-tetrahydro-naphthalen-1-yloxy}-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-ylmethyl esterYield 109.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (8.8 μL, 0.13 mmol) was added to a solution of Intermediate 14g (50 mg, 0.08 mmol) and DIPEA (46 μL, 0.26 mmol) in DCM (1.5 mL) and the reaction mixture was stirred at RT for 1 h. The mixture was diluted with DCM (5 mL) and washed with water (3×5 mL). The organic layer was passed through a phase separator and concentrated in vacuo to afford the title compound (57 mg, 100%). LCMS (Method 3): Rt: 3.21 min, m/z 651 [MH+].

Workup

  1. washwashed with water (3×5 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5c7a33b2b04429cad29ed424935e6e2
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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