Hydrochloric Acid → HCID 58169579, compound

HRID 1484883Notes

Reaction equation

HRID 1484883 reaction equation
[Cl:1][C:2]1[C:3]([NH:27][C:28]2[CH:32]=[C:31]([CH:33]3[CH2:35][CH2:34]3)[NH:30][N:29]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.Cl.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[NH2:19][CH2:18][CH2:17][NH:16][S:13]([C:11]1[S:12][C:8]([C:5]2[N:4]=[C:3]([NH:27][C:28]3[CH:32]=[C:31]([CH:33]4[CH2:34][CH2:35]4)[NH:30][N:29]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:9][CH:10]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 58169455HCID 58169455, compound2×

Product 1

HCID 58169579HCID 58169579, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamido)ethylcarbamate (Compound 78) (70 mg, 12.96 mmol, 1 equiv.) was added into HCl in MeOH and the resulting mixture was stirred at room temperature for 2 h. The mixture was adjusted pH10 with Na2CO3, and extracted with EA (50 mL×3). The organic phase was combined and washed with brine, dried (Na2SO4), evaporated to afford N-(2-aminoethyl)-5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 75) (38.3 mg, 67%). LC-MS (m/z)=440 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.81-0.82 (m, 2H), 1.03-1.05 (m, 2H), 2.01-2.03 (m, 1H), 2.90 (q, J=5.6 Hz, 2H), 3.15 (q, J=6.0 Hz, 2H), 6.43 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.85 (d, J=3.6 Hz, 1H), 8.18 (s, 1H), 8.48 (d, J=5.6 Hz, 1H), 8.55 (s, 1H), 9.83 (d, J=20.8 Hz, 1H)

Workup

  1. extractionextracted with EA (50 mL×3)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-45134369ca6245afb576a2bb88e44384
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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