4-tert-Butylbenzoyl chloride → Hydrochloric Acid

HRID 1050509Notes

Reaction equation

HRID 1050509 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:17]=[C:18]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]4)[N:19]=[N:20][C:21]=3[C:22]([NH2:24])=[O:23])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:41]([C:45]1[CH:53]=[CH:52][C:48]([C:49]([Cl:51])=[O:50])=[CH:47][CH:46]=1)([CH3:44])([CH3:43])[CH3:42]>CN1C(=O)CCC1>[C:41]([C:45]1[CH:46]=[CH:47][C:48]([C:49]([N:28]2[CH2:29][CH2:30][CH2:31][C@@H:26]([NH:25][C:18]3[N:19]=[N:20][C:21]([C:22]([NH2:24])=[O:23])=[C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[O:8])=[CH:10][CH:11]=4)[N:17]=3)[CH2:27]2)=[O:50])=[CH:52][CH:53]=1)([CH3:44])([CH3:42])[CH3:43].[ClH:51]

Participants

6

Reactant 3

HCID 743724-tert-Butylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 118115044US9656988, Example 61

Product 2

HCID 313Hydrochloric AcidHCID 118115274US9656988, Example 62

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (R)-5-(4-(morpholine-4-carbonyl)phenylamino)-3-(piperidin-3-ylamino)-1,2,4-triazine-6-carboxamide (75) HCl salt (60 mg, 0.13 mmol) in NMP (3 mL) was added DIEA (90 μL, 0.76 mmol) and then 4-tert-butylbenzoyl chloride (39 mg, 0.20 mmol). The mixture was stirred at RT for 20 min, quenched with TFA (0.1 mL), diluted with 2 mL water, and subjected to reverse phase preparative HPLC to afford the title compound (76) as an HCl salt. MS found for C31H38N8O4 as (M+H)+ 587.2, (M−H)− 585.2. UV: λ=268, 287 nm.

Workup

  1. customquenched with TFA (0.1 mL)
  2. additiondiluted with 2 mL water

Sources & evidence

ORD record
ord-64f0bedcba7942309708df2b327bec4b
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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