HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methanamine, hydrochloride (1:1) → 2-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-phenoxy]-N-methylacetamide

HRID 1926376
Notes
Print preview

Reaction equation

HRID 1926376 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14](O)=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[Cl-].C[NH3+].[CH3:31][N:32](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([NH:32][CH3:31])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 675208764-[6-Amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetic acid

Product 1

HCID 675212432-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-phenoxy]-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetic acid (20 mg, 0.050 mmol) in DMF (1.0 mL) were added methylammonium chloride (4 mg, 0.06 mmol), TBTU (19 mg, 0.060 mmol) and DIEA (0.05 mL, 0.3 mmol). The mixture was left to stir at rt for 30 min. Purification via MDP afforded the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.67 (d, J=4.8 Hz, 3H), 4.51 (s, 2H), 7.04-7.10 (m, 2H), 7.45-7.52 (m, 1H), 7.54-7.59 (m, 1H), 7.63-7.68 (m, 2H), 7.97 (s, 2H), 8.10 (d, J=7.8 Hz, 1H), 8.13-8.17 (m, 2H), 8.48 (d, J=2.3 Hz, 1H). MS (ES+): m/z=391.10 (100) [MH+]. HPLC: tR=3.20 min (ZQ3, polar—5 min).

Workup

  1. waitThe mixture was left
  2. customPurification via MDP

Sources & evidence

ORD record
ord-1282a154c961494f966a040a4fe28ff7
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178668B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes