(1H-pyrazol-1-yl)methanediamine hydrochloride → HCID 178439346, compound

HRID 45705Notes

Reaction equation

HRID 45705 reaction equation
[NH2:1][CH2:2]/[C:3](/[CH3:29])=[CH:4]/[C:5]1[CH:26]=[C:25]([F:27])[C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:7]([F:28])[CH:6]=1.Cl.[N:31]1([CH:36](N)[NH2:37])C=CC=N1>C1COCC1>[F:28][C:7]1[CH:6]=[C:5](/[CH:4]=[C:3](\[CH3:29])/[CH2:2][NH:1][C:36]([NH2:37])=[NH:31])[CH:26]=[C:25]([F:27])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])(=[O:17])=[O:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 55285438(1H-pyrazol-1-yl)methanediamine hydrochlorideHCID 67454848(E)-4-(4-(3-amino-2-methylprop-1-enyl)-2,6-difluorophenoxy)-N-(2-(dimethylamino)ethyl)benzenesulfonamide2×

Product 1

HCID 178439346HCID 178439346, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-4-(4-(3-amino-2-methylprop-1-enyl)-2,6-difluorophenoxy)-N-(2-(dimethylamino)ethyl)benzenesulfonamide (Intermediate 93.4, 39.3 mg, 0.092 mmol) in dry THF (460 uL, 0.2M) under N2 was added TEA (0.276 mmol, 27.9 mg) and (1H-pyrazol-1-yl)methanediamine hydrochloride (0.102 mmol, 14.9 mg). The resulting solution was stirred for 1 hour, at which point LCMS indicated complete conversion. The solvent was removed and the resulting residue brought up in 1:1 ACN:water and purified by preparative HPLC to give 16.9 mg of the title compound (26%) as a TFA salt. 1H-NMR (400 MHz, CD4OD): δ 7.87 (d, 2H), 7.12 (d, 2H), 7.08 (d, 2H), 3.92 (s, 2H), 3.62 (m, 2H), 3.29 (m, 2H), 3.17 (t, 2H), 2.01 (s, 6H), 1.91 (s, 3H). MS (m/z): 468.12 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customwater and purified by preparative HPLC

Sources & evidence

ORD record
ord-f1ae7cebc96a4484b4fdef0434cfff50
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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