Sodium Chloride → [(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylate

HRID 384671Notes

Reaction equation

HRID 384671 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25]2[C:30]([C:31]([OH:33])=[O:32])=[CH:29][N:28]=[C:27]([NH:34][C:35]3[CH:40]=[N:39][C:38]([C:41]#[N:42])=[CH:37][N:36]=3)[CH:26]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(O[N:51]1N=N[C:53]2C=CC=[N:57][C:52]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O/N=C(/N)\C.[Na+].[Cl-]>CN(C=O)C>[NH2:57]/[C:52](=[N:51]/[O:32][C:31]([C:30]1[C:25]([NH:24][CH2:23][CH:20]2[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:16])[CH2:22][CH2:21]2)=[CH:26][C:27]([NH:34][C:35]2[CH:40]=[N:39][C:38]([C:41]#[N:42])=[CH:37][N:36]=2)=[N:28][CH:29]=1)=[O:33])/[CH3:53]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 536066422059-22-9HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 596134654-((1-(Tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinic acid

Product 1

HCID 59613429[(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DIPEA (96 μL, 0.55 mmol) was added to a solution of 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinic acid (Synthesis 75-A) (50 mg, 0.11 mmol), HATU (54 mg, 0.14 mmol) in DMF (6 mL) under argon. The reaction mixture was stirred for 15 min at r.t. and (E)-N′-hydroxyacetimidamide (25 mg, 0.34 mmol) in DMF (0.5 mL) was added. The resulting solution was stirred at r.t. for 12 hr. Aqueous NaCl solution (15 mL) was added and the resulting precipitate was collected. The solid was washed with water and n-hexane to give a yellow powder (43 mg, 77%).

Workup

  1. stirringThe resulting solution was stirred at r.t. for 12 hr
  2. customthe resulting precipitate was collected
  3. washThe solid was washed with water and n-hexane

Sources & evidence

ORD record
ord-3b5f3b6745004473a25c317baf6eb4fe
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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