Ammonia → HCID 86689764, compound

HRID 1396414Notes

Reaction equation

HRID 1396414 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OCC)=[O:9])=[C:4]([NH:13][C:14]2[N:19]=[C:18]3[CH2:20][CH2:21][CH2:22][C:17]3=[CH:16][CH:15]=2)[CH:3]=1.CO.[NH3:25]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:25])=[O:9])=[C:4]([NH:13][C:14]2[N:19]=[C:18]3[CH2:20][CH2:21][CH2:22][C:17]3=[CH:16][CH:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689763ethyl 6-chloro-4-(6,7-dihydro-5H-cyclopenta[b]pyridin-2-ylamino)pyridazine-3-carboxylate

Product 1

HCID 86689764HCID 86689764, compoundYield 75%

Procedure

Ethyl 6-chloro-4-(6,7-dihydro-5H-cyclopenta[b]pyridin-2-ylamino)pyridazine-3-carboxylate (554 mg, 1.74 mmol) was suspended in ammonia 7M in methanol (11.8 g, 15.0 mL, 105 mmol). The flask containing the mixture was sealed and stirred at room temperature for 18 h. The precipitated off-white solid was separated by filtration and dried under high vacuum to give 6-chloro-4-(6,7-dihydro-5H-cyclopenta[b]pyridin-2-ylamino)pyridazine-3-carboxamide (375 mg, 75%) as an off-white solid. 1H NMR (DMSO-d6) δ: 11.92 (s, 1H), 8.95 (s, 1H), 8.83 (s, 1H), 8.18 (s, 1H), 7.63 (d, J=7.9 Hz, 1H), 6.84 (d, J=7.9 Hz, 1H), 2.78-3.00 (m, 4H), 2.07 (quin, J=7.6 Hz, 2H); LC-MS 290.0 [M+H]+.

Workup

  1. additionThe flask containing the mixture
  2. customwas sealed
  3. customThe precipitated off-white solid was separated by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-6e6d937eded14545be4ce2503a8766bb
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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