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Diisopropylethylamine → (R)-6-bromo-4-(2,2-dimethylcyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408951
Notes
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Reaction equation

HRID 1408951 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[CH3:15][C:16]1([CH3:22])[CH2:20][CH2:19][CH2:18][C@H:17]1[NH2:21].C(C1C=NN2C=C(C(OCC)=O)C=C2C=1N[C@@H]1CCCC1(C)C)(=O)N.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:21][C@@H:17]3[CH2:18][CH2:19][CH2:20][C:16]3([CH3:22])[CH3:15])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15196533(1R)-2,2-dimethylcyclopentan-1-amineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 68358891(R)-Ethyl 3-carbamoyl-4-((2,2-dimethylcyclopentyl)amino)pyrrolo[1,2-b]pyridazine-6-carboxylate

Product 1

HCID 68291536(R)-6-bromo-4-(2,2-dimethylcyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide
Yield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 300 mg, 1.093 mmol) and (R)-2,2-dimethylcyclopentanamine (from Step 3 of Intermediate 5, 164 mg, 1.093 mmol) in DMF (4 mL) was added DIPEA (0.573 mL, 3.28 mmol). The mixture was heated at 120° C. for 60 min in a microwave reactor. Water (4 volumes) was added and the resulting suspension was stirred for 1 h. The solids were filtered, rinsed with water (2×), and then dried to afford the title compound (324 mg, 84% yield) as a pale yellow solid. HPLC (conditions 0): retention time=4.07 min; LCMS: 351.01 (M+), 353.00 (M+2); 1H NMR (methanol-d4, 400 MHz) δ 8.14 (s, 1H), 7.62 (d, J=1.8 Hz, 1H), 7.02 (d, J=1.8 Hz, 1H), 4.15 (t, J=7.3 Hz, 1H), 2.32 (m, 1H), 1.61-1.86 (m, 5H), 1.13 (s, 3H), 1.10 (s, 3H).

Workup

  1. filtrationThe solids were filtered
  2. washrinsed with water (2×)
  3. customdried

Sources & evidence

ORD record
ord-ef1eff6f9e524de8b1245621b1fd47aa
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921368B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes