tert-Butanol → Tert-butyl [6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

HRID 1663695Notes

Reaction equation

HRID 1663695 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][CH:33]=1)[C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23](C(O)=O)[N:24]=2)[N:21]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1.C([N:53]([CH2:56]C)CC)C.[C:58]([OH:62])([CH3:61])([CH3:60])[CH3:59]>>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][CH:33]=1)[C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[C:23]([NH:53][C:56](=[O:41])[O:62][C:58]([CH3:61])([CH3:60])[CH3:59])[N:24]=2)[N:21]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 575054566-(3-{[3-(1-Cyano-1-methylethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid

Product 1

HCID 57505457Tert-butyl [6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamateYield 71%

Procedure

Using 6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid (826 mg, 1.87 mmol), diphenylphosphoryl azide (771 mg, 2.81 mmol), triethylamine (381 mg, 3.74 mmol) and tert-butanol (30.0 mL), and in the same manner as in Example 64, the title compound (682 mg, 71%) was obtained as a white powder.

Sources & evidence

ORD record
ord-91849cfb6a8b452fbdbc8b16d4807704
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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